40 2 Polyfunctional Lithium <strong>Organometallics</strong> for Organic Synthesis 70 M. D. B. Fenster, B. O. Patrick, G. R. Dake, Org. Lett. 2001, 3, 2109±2112. 71 For a review, see: R. Ch<strong>in</strong>chilla, C. Nµjera, M. Yus, Chem. Rev. 2004, 104, 2667±2722. 72 K. Worm, F. Chu, K. Matsumoto, M. D. Best, V. Lynch, E. V. Anslyn, Chem. Eur. J. 2003, 9, 741±747. 73 P. Calí, M. Begtrup, Tetrahedron 2002, 58, 1595±1605. 74 A. Dondoni, A. Marra, M. Mizuno, P. P. Giovann<strong>in</strong>i, J. Org. Chem. 2002, 67, 4186±4199. 75 For reviews, see: (a) N. Sotomayor, E. Lete, Curr. Org. Chem. 2003, 7, 1±26. (b) C. Nµjera, J. M. Sansano, M. Yus, Tetrahedron 2003, 59, 9255±9303. 76 J. Chun, L. He, H.-S. Byun, R. Bittman, J. Org. Chem. 2000, 65, 7634±7640. 77 C. Fruit, A. Turck, N. PlØ, L. Mojovic, G. QuØgu<strong>in</strong>er, Tetrahedron 2001, 57, 9429±9435. 78 (a) O. Sugimoto, M. Sudo, K. Tanji, Tetrahedron Lett. 1999, 40, 2139±2140. (b) O. Sugimoto, M. Sudo, K. Tanji, Tetrahedron 2001, 57, 2133±2138. 79 M. Shimizu, T. Kurahashi, T. Hiyama, J. Synth. Org. Chem. Jpn. 2001, 59, 1062±1069. 80 A. Kasatk<strong>in</strong>, R. J. Whitby, Tetrahedron Lett. 1997, 38, 4857±4860. 81 G. Köbrich, H. Trapp, I. Hornke, Tetrahedron Lett. 1964, 1131±1136. 82 F. Tellier, R. Sauv†tre, J. F. Normant, Y. Dromzee, Y. Jeann<strong>in</strong>, J. Organomet. Chem. 1987, 331, 281±298. 83 (a) F. Foubelo, M. Yus, Rev. Heteroatom Chem. 1997, 17, 73±107. (b) M. Yus, F. Foubelo, Targets Heterocycl. Syst. 2002, 6, 136±171. (c) M. Yus, Pure Appl. Chem. 2003, 75, 1453±1475. 84 (a) J. Barluenga, F. J. Faæanµs, M. Yus, G. Asensio, Tetrahedron Lett. 1978, 2015±2016. (b) J. Barluenga, F. J. Faæanµs, M. Yus, J. Org. Chem. 1979, 44, 4798±4801. (c) J. Barluenga, F. J. Faæanµs, J. Villamaæa, M. Yus, J. Org. Chem. 1982, 47, 1560±1564. 85 (a) T. Soler, A. Bachki, L. R. Falvello, F. Foubelo, M. Yus, Tetrahedron: Asymmetry 1998, 9, 3939±3943. (b) T. Soler, A. Bachki, L. R. Falvello, F. Foubelo, M. Yus, Tetrahedron: Asymmetry 2000, 11, 493±517. 86 C. Nµjera, M. Yus, D. Seebach, Helv. Chim. Acta 1984, 67, 289±300. 87 (a) F. Foubelo, A. GutiØrrez, M. Yus, Tetrahedron Lett. 1997, 38, 4837±4840. (b) F. Foubelo, A. GutiØrrez, M. Yus, Synthesis 1999, 503±514. 88 R. E. Conrow, Tetrahedron Lett. 1993, 34, 5553±5554. 89 D. Behnke, L. Hennig, M. F<strong>in</strong>deisen, P. Welzel, D. Müller, M. Thormann, H.-J. H<strong>of</strong>mann, Tetrahedron 2000, 56, 1081±1095. 90 (a) A. Bachki, F. Foubelo, M. Yus, Tetrahedron: Asymmetry 1995, 6, 1907±1910. (b) A. Bachki, F. Foubelo, M. Yus, Tetrahedron: Asymmetry 1996, 7, 2997±3008. 91 (a) L. R. Falvello, F. Foubelo, T. Soler, M. Yus, Tetrahedron: Asymmetry 2000, 11, 2063±2066. (b) M. Yus, T. Soler, F. Foubelo, Tetrahedron: Asymmetry 2001, 12, 801±810. 92 (a) J. Barluenga, M. Yus, P. Bernad, J. Chem. Soc., Chem. Commun. 1978, 847. (b) J. Barluenga, M. Yus, J. M. Concellón, P. Bernad, J. Chem. Research (S) 1980, 41. (c) J. Barluenga, M. Yus, J. M. Concellón, P. Bernad, J. Org. Chem. 1981, 46, 2721±2726. (d) J. Barluenga, M. Yus, J. M. Concellón, P. Bernad, J. Org. Chem. 1983, 48, 609±611. 93 (a) J. Almena, F. Foubelo, M. Yus, Tetrahedron Lett. 1993, 34, 1649±1652. (b) J. Almena, F. Foubelo, M. Yus, J. Org. Chem. 1994, 59, 3210±3215. 94 (a) F. Foubelo, M. Yus, Tetrahedron Lett. 1994, 35, 4831±4834. (b) F. Foubelo, M. Yus, Tetrahedron: Asymmetry 1996, 7, 2911±2922. 95 M. N. Kenworthy, J. P. Kilburn, R. J. K. Taylor, Org. Lett. 2004, 6, 19±22. 96 Y. S. Park, P. Beak, Tetrahedron 1996, 52, 12333±12350. 97 F. Taherirastgar, L. Brandsma, Chem. Ber. 1997, 130, 45±48. 98 P. Langer, M. Dör<strong>in</strong>g, D. Seyferth, H. Görls, Chem. Eur. J. 2001, 7, 573±584. 99 A. Armstrong, F. W. Goldberg, D. A. Sandham, Tetrahedron Lett. 2001, 42, 4585±4587. 100 J. Tholander, J. Bergman, Tetrahedron 1999, 55, 12595±12602.
101 M. Schlosser, H. Wei, Tetrahedron 1997, 53, 1735±1742. 102 K. Takeda, H. Haraguchi, Y. Okamoto, Org. Lett. 2003, 5, 3705±3707. 103 C. Yip, S. Handerson, G. K. Tranmer, W. Tam, J. Org. Chem. 2001, 66, 276±286. 104 For reviews, see: (a) W. E. Parham, C. K. Bardher, Acc. Chem. Res. 1982, 15, 300±305. (b) P. Beak, V. Snieckus, Acc. Chem. Res. 1982, 15, 306±312. 105 K. Yamada, T. Kurokawa, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2003, 125, 6630±6631. 106 J. Barluenga, F. Foubelo, F. J. Faæanµs, M. Yus, J. Chem. Soc., Perk<strong>in</strong> Trans. 1 1989, 553±557. 107 X. Han, E. J. Corey, Org. Lett. 1999, 1, 1871±1872. 108 (a) L. A. Paquette, L. H. Kuo, A. T. Hamme, R. Kreuzholz, J. Doyon, J. Org. Chem. 1997, 62, 1730±1736. (b) J.-K. Ergüden, H. W. Moore, Org. Lett. 1999, 1, 375±378. 109 T. J. Donohoe, K. Blades, M. Helliwell, M. J. War<strong>in</strong>g, N. J. Newcombe, Tetrahedron Lett. 1998, 39, 8755±8758. 110 (a) J. Barluenga, R. Sanz, A. Granados, F. J. Faæanµs, J. Am. Chem. Soc. 1998, 120, 4865±4866. (b) F. J. Faæanµs, A. Granados, R. Sanz, J. M. Ignacio, J. Barluenga, Chem. Eur. J. 2001, 7, 2896±2907. 111 A. Bachki, F. Foubelo, M. Yus, Tetrahedron 1997, 53, 4921±4934. 112 J. Aigner, E. Göss<strong>in</strong>ger, H. Kählig, G. Menz, K. Pflugseder, Angew. Chem. Int. Ed. 1998, 37, 2226±2228. 113 M. E. Fox, C. Li, J. P. Mar<strong>in</strong>o, L. E. Overman, J. Am. Chem. Soc. 1999, 121, 5467±5480. 114 S. P. Götzö, D. Seebach, J.-J. Sanglier, Eur. J. Org. Chem. 1999, 2533±2544. 115 C. Mück-Lichtenfeld, H. Ahlbrecht, Tetrahedron 1999, 55, 2609±2642. 116 S. Norsikian, I. Marek, S. Kle<strong>in</strong>, J. F. Poisson, J. F. Normant, Chem. Eur. J. 1999, 5, 2055±2068. 117 B. Mudryk, T. Cohen, J. Org. Chem. 1991, 56, 5760±5761. 118 A. Bachki, L. R. Falvello, F. Foubelo, M. Yus, Tetrahedron: Asymmetry 1997, 8, 2633±2643. 119 U. Azzena, L. Pilo, Synthesis 1999, 664±668. References 41 120 (a) J. Almena, F. Foubelo, M. Yus, Tetrahedron 1997, 53, 5563±5572. (b) J. Almena, F. Foubelo, M. Yus, Tetrahedron 1994, 50, 5775±5782. 121 L. Garamszegi, M. Schlosser, Angew. Chem. Int. Ed. 1998, 37, 3173±3175. 122 For a review, see: I. Kuwajima, E. Nakamura, Top. Curr. Chem. 1990, 115, 1±39. 123 I. M. Pastor, M. Yus, Tetrahedron Lett. 2001, 42, 1029±1032. 124 S. Zhu, T. Cohen, Tetrahedron 1997, 53, 17607±17624. 125 X. Feng, M. O. Senge, J. Chem. Soc., Perk<strong>in</strong> Trans. 1 2001, 1030±1038. 126 N. Bremand, I. Marek, J. F. Normant, Tetrahedron Lett. 1999, 40, 3383±3386. 127 For reviews, see: (a) P. Beak, A. I. Meyers, Acc. Chem. Res. 1986, 19, 356±363. (b) M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem. Int. Ed. 2004, 43, 2206±2225. 128 D. J. Pippel, M. D. Curtis, H. Du, P. Beak, J. Org. Chem. 1998, 63, 2±3. 129 M. Yus, T. Soler, F. Foubelo, J. Org. Chem. 2001, 66, 6207±6208. 130 For reviews. see: (a) H. Ahlbrecht, U. Beyer, Synthesis 1999, 365±390. (b) A. R. Katritzky, M. Piffl, H. Lang, E. Anders, Chem. Rev. 1999, 99, 665±722. 131 K. Behrens, R. Fröhlich, O. Meyer, D. Hoppe, Eur. J. Org. Chem. 1998, 2397±2403. 132 R. Tiedemann, F. Narjes, E. Schaumann, Synlett 1994, 594±596. 133 M. Lombardo, S. Spada, C. Tromb<strong>in</strong>i, Eur. J. Org. Chem. 1998, 2361±2364. 134 H. Ahlbrecht, P. Weber, Synthesis 1992, 1018±1025. 135 H. Ahlbrecht, R. Schmidt, U. Beyer, Eur. J. Org. Chem. 1998, 1371±1377. 136 J. Barluenga, F. J. Faæanµs, F. Foubelo, M. Yus, J. Chem. Soc., Chem. Commun. 1988, 1135±1136. 137 A. Krief, W. Dumont, Tetrahedron Lett. 1997, 38, 657±660. 138 S. Harder, M. Lutz, A. Streitwieser, J. Am. Chem. Soc. 1995, 117, 2361±2362. 139 U. Azzena, S. Carta, G. Melloni, A. Sechi, Tetrahedron 1997, 53, 16205±16212. 140 C. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054±4055.
- Page 2 and 3:
Organometallics. Paul Knochel Copyr
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Handbook of Functionalized Organome
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Contents Preface XV List of Authors
- Page 8 and 9: Contents 3.3.9 Oxidation of Functio
- Page 10 and 11: 6.3.1 Nucleophilic Addition onto Ca
- Page 12 and 13: 9.2.3 Preparation of Functionalized
- Page 14 and 15: 13.6.4 Nickel-Catalyzed Cross-coupl
- Page 16 and 17: Preface Since the pioneering work o
- Page 18 and 19: XVIII List of Authors Corinne Gosmi
- Page 20 and 21: 1 Introduction Paul Knochel and Fel
- Page 22 and 23: umorganic is directly generated in
- Page 24 and 25: Et H 21 Et AlBu 2 + CO 2Et Cu(CN)Mg
- Page 26 and 27: 8 2 Polyfunctional Lithium Organome
- Page 28 and 29: 10 2 Polyfunctional Lithium Organom
- Page 30 and 31: R R 12 2 Polyfunctional Lithium Org
- Page 32 and 33: MeO MeO R 14 2 Polyfunctional Lithi
- Page 34 and 35: N 16 2 Polyfunctional Lithium Organ
- Page 36 and 37: 18 2 Polyfunctional Lithium Organom
- Page 38 and 39: Li LiO 20 2 Polyfunctional Lithium
- Page 40 and 41: Li 22 2 Polyfunctional Lithium Orga
- Page 42 and 43: 24 2 Polyfunctional Lithium Organom
- Page 44 and 45: 26 Ph O Ni-Pr 2 2 Polyfunctional Li
- Page 46 and 47: 28 Li 2 Polyfunctional Lithium Orga
- Page 48 and 49: 30 2 Polyfunctional Lithium Organom
- Page 50 and 51: Li 32 203 2 Polyfunctional Lithium
- Page 52 and 53: 34 2 Polyfunctional Lithium Organom
- Page 54 and 55: 36 Br 2 Polyfunctional Lithium Orga
- Page 56 and 57: 38 2 Polyfunctional Lithium Organom
- Page 60 and 61: 42 2 Polyfunctional Lithium Organom
- Page 62 and 63: 3 Functionalized Organoborane Deriv
- Page 64 and 65: Br SSiMe 2tBu 4 3.2 Preparation and
- Page 66 and 67: B O O 3.2 Preparation and Reaction
- Page 68 and 69: 3.2 Preparation and Reaction of Fun
- Page 70 and 71: 3.2 Preparation and Reaction of Fun
- Page 72 and 73: Ar H Ar = O HB O CF 3 CF 3 3.2 Prep
- Page 74 and 75: 3.2 Preparation and Reaction of Fun
- Page 76 and 77: X X Cl Cl TfO Cl 3.2 Preparation an
- Page 78 and 79: HO HO Br OH O X N N O N 3.2 Prepara
- Page 80 and 81: MOMO MOMO I CbzN O 3.2 Preparation
- Page 82 and 83: 3.2 Preparation and Reaction of Fun
- Page 84 and 85: (HO) 3B O NMe 3 N N O Br 3.2 Prepar
- Page 86 and 87: H H O O N H N H O OEt O O OEt O 3.2
- Page 88 and 89: t BuO2C O N H 3.2 Preparation and R
- Page 90 and 91: 3.2 Preparation and Reaction of Fun
- Page 92 and 93: 3.2 Preparation and Reaction of Fun
- Page 94 and 95: 3.2 Preparation and Reaction of Fun
- Page 96 and 97: R H2O R R B(OH) 2 B(OH) 2 3.3 Prepa
- Page 98 and 99: 3.3 Preparation and Reactions of Fu
- Page 100 and 101: R 124 BF 3K Br 3.3 Preparation and
- Page 102 and 103: B O O I OR O OR O O O O O OR 3.3 Pr
- Page 104 and 105: S N O B O I O 133 3.4 Preparation a
- Page 106 and 107: 3.5 Synthesis and Reactions of Func
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3.7 Synthesis and Reactions of Func
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3.7 Synthesis and Reactions of Func
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3.7 Synthesis and Reactions of Func
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3.7 Synthesis and Reactions of Func
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R TrocO S N R 1 O S N 13 12 O 1 160
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3.7 Synthesis and Reactions of Func
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3.7 Synthesis and Reactions of Func
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22 H. Nakamura, M. Fujiwara, Y. Yam
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102 K. A. Scheidt, A. Tasaka, T. D.
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4 Polyfunctional Magnesium Organome
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crystallize with four-coordinated M
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4.2Methods of Preparation of Grigna
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4.2Methods of Preparation of Grigna
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4.2Methods of Preparation of Grigna
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NC Br Br 4.2Methods of Preparation
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N N Ph I 4.2Methods of Preparation
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4.2Methods of Preparation of Grigna
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4.2Methods of Preparation of Grigna
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Cl MgBr 4.2Methods of Preparation o
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4.2Methods of Preparation of Grigna
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4.2Methods of Preparation of Grigna
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4.2Methods of Preparation of Grigna
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4.2Methods of Preparation of Grigna
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4.2Methods of Preparation of Grigna
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4.2Methods of Preparation of Grigna
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O O O O 4.2Methods of Preparation o
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O Me Me O Pent I 4.2Methods of Prep
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4.2Methods of Preparation of Grigna
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4.3 Further Applications of Functio
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4.3 Further Applications of Functio
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4.3 Further Applications of Functio
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OTIPS I iPrMgCl OTIPS 4.3 Further A
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4.4 Application of Functionalized M
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I O O OBn Pd(t-Bu 3P) 2 (10 mol%) 4
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4.4 Application of Functionalized M
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Me OTf CO2Et + Me 4.4 Application o
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4.4 Application of Functionalized M
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12 a) F. Bickelhaupt in H. G. Riche
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56 G. Varchi, C. Kofink, D. M. Lind
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kin Trans. 1 1992, 1393; b) M. Sato
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31, 805; J. F. Hartwig, Angew. Chem
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5 Polyfunctional Silicon Organometa
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stereocontrol [5]. Similar chiral c
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5.2 Allylic Silanes seven-membered
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SiMe 3 33 Pr OH OSiMe 3 SiMe 3 34 O
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5.2 Allylic Silanes Although alkyl
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R O Si H 60a (R = H) 60b (R = Me) R
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Bpin SiMe 2Ph (CH 2) 2Ph 73 EtCH(OE
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BnO HO SiMe2Ph 2 BnO CHO BnO O BF3
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5.3 Alkenylsilanes When the same st
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HO I O Si Mo cat. : m n I O Si 111
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5.4Alkylsilanes Transition metal-ca
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5.4Alkylsilanes The fluoride-induce
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5.5 Miscellaneous Preparations and
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5.5 Miscellaneous Preparations and
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716. (c)I. E. Markó, J.-M. Planche
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6 Polyfunctional Tin Organometallic
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phine ligand or Pd II (PPh 3) 2Cl 2
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Bu 3 Sn Scheme 6.4 n-Pent + Me I O
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N N N H 2 I Scheme 6.8 N + Me Sn 3
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O O O NaO HO Me P O OH O OH (+)-Fos
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6.2 Metal-Catalyzed Coupling Reacti
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6.2 Metal-Catalyzed Coupling Reacti
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6.3 Nucleophilic Additions a-hydrox
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6.3 Nucleophilic Additions oxy alde
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6.3 Nucleophilic Additions found ap
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6.3 Nucleophilic Additions 6.3.1.5.
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6.3 Nucleophilic Additions ethylami
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N H 91% (ee:84%) Scheme 6.31 N CO 2
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6.4 Radical Reactions of Organotins
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TsN Scheme 6.37 + Bu 3Sn O Ph AIBN
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6.5.2 Tin-to-lithium Exchange 6.5.2
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Ar OR Scheme 6.42 N H SnBu 3 n-BuLi
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References 1 D. Azarian, S. S. Dua,
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Commun., 2002, 2608±2609; W. Su, S
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110 Y. Obora, M. Nakanishi, M. Toku
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178 Y. Yamamoto, H. Yatagai, Y. Nar
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J. Chem. Soc., Chem. Commun., 1995,
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301 D. P. G. Hamon, R. A. Massy-Wes
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371 I. D. Gridnev, O. L. Tok, N. A.
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252 7 Polyfunctional Zinc Organomet
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254 7 Polyfunctional Zinc Organomet
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256 7 Polyfunctional Zinc Organomet
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258 7 Polyfunctional Zinc Organomet
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BnO H Me 37 :1:1mixtureof diastereo
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262 Me 3Si 7 Polyfunctional Zinc Or
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264 F F 7 Polyfunctional Zinc Organ
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266 7 Polyfunctional Zinc Organomet
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Bu S O IZn(CH 2) 4ZnI 94 268 7 Poly
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270 7 Polyfunctional Zinc Organomet
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OAc MeO I EtO 2C 272 CHO S C N 7 Po
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274 7 Polyfunctional Zinc Organomet
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276 O 7 Polyfunctional Zinc Organom
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278 7 Polyfunctional Zinc Organomet
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280 E 7 Polyfunctional Zinc Organom
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282 MeO 2C O I 7 Polyfunctional Zin
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H Ph 284 7 Polyfunctional Zinc Orga
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286 7 Polyfunctional Zinc Organomet
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288 Ph N 214 O 7 Polyfunctional Zin
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290 7 Polyfunctional Zinc Organomet
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292 7 Polyfunctional Zinc Organomet
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294 IZn AcO 7 Polyfunctional Zinc O
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296 7 Polyfunctional Zinc Organomet
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298 7 Polyfunctional Zinc Organomet
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300 7 Polyfunctional Zinc Organomet
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302 7 Polyfunctional Zinc Organomet
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304 7 Polyfunctional Zinc Organomet
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306 7 Polyfunctional Zinc Organomet
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308 7 Polyfunctional Zinc Organomet
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O 310 7 Polyfunctional Zinc Organom
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312 7 Polyfunctional Zinc Organomet
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314 7 Polyfunctional Zinc Organomet
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316 7 Polyfunctional Zinc Organomet
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318 AcO 7 Polyfunctional Zinc Organ
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EtO 2C 320 MeO 7 Polyfunctional Zin
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MeO O 322 n-Hept O O I Me 7 Polyfun
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MeO 462 324 460 Br I 463 7 Polyfunc
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326 7 Polyfunctional Zinc Organomet
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328 7 Polyfunctional Zinc Organomet
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330 7 Polyfunctional Zinc Organomet
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332 7 Polyfunctional Zinc Organomet
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334 7 Polyfunctional Zinc Organomet
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336 7 Polyfunctional Zinc Organomet
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338 7 Polyfunctional Zinc Organomet
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340 7 Polyfunctional Zinc Organomet
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342 7 Polyfunctional Zinc Organomet
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344 7 Polyfunctional Zinc Organomet
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346 7 Polyfunctional Zinc Organomet
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348 8 Polyfunctional 1,1-Organodime
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350 O 8 Polyfunctional 1,1-Organodi
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352 8 Polyfunctional 1,1-Organodime
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354 8 Polyfunctional 1,1-Organodime
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356 8 Polyfunctional 1,1-Organodime
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358 8 Polyfunctional 1,1-Organodime
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360 8 Polyfunctional 1,1-Organodime
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CH 2(ZnI) 2 4 362 8 Polyfunctional
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364 8 Polyfunctional 1,1-Organodime
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366 8 Polyfunctional 1,1-Organodime
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368 8 Polyfunctional 1,1-Organodime
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370 8 Polyfunctional 1,1-Organodime
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372 8 Polyfunctional 1,1-Organodime
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374 8 Polyfunctional 1,1-Organodime
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376 8 Polyfunctional 1,1-Organodime
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9 Polyfunctional Organocopper Reage
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S 5 CuI·LiCl Cu(CN)Li Li naphthale
- Page 398 and 399:
Br CO 2Et I CO 2Et CO 2Et Np 2CuLi
- Page 400 and 401:
9.2 Preparation of Functionalized O
- Page 402 and 403:
Pent I O O Pent I CO 2Et O Br Pent
- Page 404 and 405:
Ph Ph N OMe 1) n-BuLi 2) alkynylcop
- Page 406 and 407:
9.3 Applications of Functionalized
- Page 408 and 409:
PrCu·MgBr 2·SMe 2 Pr Me H Pr H HO
- Page 410 and 411:
19 X. Yang, T. Rotter, C. Piazza, P
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n-C 7H 15 398 10 Functional Organon
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400 10 Functional Organonickel Reag
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402 10 Functional Organonickel Reag
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404 10 Functional Organonickel Reag
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406 10 Functional Organonickel Reag
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408 10 Functional Organonickel Reag
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410 10 Functional Organonickel Reag
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412 10 Functional Organonickel Reag
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414 10 Functional Organonickel Reag
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416 10 Functional Organonickel Reag
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418 10 Functional Organonickel Reag
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420 10 Functional Organonickel Reag
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422 10 Functional Organonickel Reag
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O 424 10 Functional Organonickel Re
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TIPSO R 1 Cp 2ClZr O H 426 O N 10 F
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428 10 Functional Organonickel Reag
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430 10 Functional Organonickel Reag
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432 10 Functional Organonickel Reag
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434 10 Functional Organonickel Reag
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436 10 Functional Organonickel Reag
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O 438 O Br 10 Functional Organonick
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440 10 Functional Organonickel Reag
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Cl 442 CN 10 Functional Organonicke
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444 10 Functional Organonickel Reag
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446 10 Functional Organonickel Reag
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448 10 Functional Organonickel Reag
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11 Polyfunctional Metal Carbenes fo
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11.2 Chromium-Templated Cycloadditi
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11.2 Chromium-Templated Cycloadditi
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(CO) 5Cr O Ph 15 1) t Bu t BuOMe, 5
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O MeO O O O O MeO O OMe Cr(CO) 5 Me
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11.2.3 Cyclization of Chromium Olig
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(CO)5Cr OR * O S + OMe 11.2 Chromiu
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[2+2+1] R 1 R 1 OH (CO) 5Cr R 2 (CO
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11.3 Reactions of Higher Nuclearity
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Br O X Br O R 2 R 2 O 85: X = Si-tB
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11.3 Reactions of Higher Nuclearity
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11.4 Metathesis Reactions Catalyzed
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R 2 R 1 O R O 3 O 11.4 Metathesis R
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i Pr i Pr i Pr Me Me (R)-160 Ph O O
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11.5 Transmetallation The dimerizat
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11.6 Metal Carbenes in Peptide Chem
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11.7 Stereoselective Syntheses with
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11.7 Stereoselective Syntheses with
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11.7 Stereoselective Syntheses with
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11.7 Stereoselective Syntheses with
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11.7 Stereoselective Syntheses with
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O O O O 100% H 2N O O O O O 311a Cr
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11.8 Sugar Metal Carbenes as Organo
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References zation reactions that al
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35 (a) C.A. Merlic, Y. You, D.M. Mc
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D. R. Cefalo, P. J. Bonitatebus Jr.
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12 Functionalized Organozirconium a
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12.2 Functionalized Organozirconoce
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Ph O (H)ZrCp Ph O 2Cl Ph O O O 92 %
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12.2 Functionalized Organozirconoce
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i-PrO O OBu-t O H N Scheme 12.15 H
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BnO Scheme 12.19 O BnO + 27 28 Cp 2
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12.2 Functionalized Organozirconoce
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R 1 O O O R R1 R 2 Scheme 12.28 R P
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12.2 Functionalized Organozirconoce
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12.3 Functionalized Organotitanium
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12.3 Functionalized Organotitanium
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t-BuOOC Scheme 12.44 O CH 3 7.5 mol
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12.3 Functionalized Organotitanium
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H 13C 6 O R Scheme 12.52 SiMe 3 O T
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12.3 Functionalized Organotitanium
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O O OEt 87 Scheme 12.59 Scheme 12.6
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12.3 Functionalized Organotitanium
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12.3 Functionalized Organotitanium
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40 A. M. Sun, X. Huang, Heteroatom
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13 Manganese Organometallics for th
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13.2.2 Preparation of Organomangane
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13.3 1,2-Addition to Aldehydes and
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13.3.2 Manganese-Mediated Barbier-
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HeptMnX + HeptMnX + Scheme 13.17 Cl
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13.4 Preparation of Ketones by Acyl
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Me 3Si Cl ( ) 3 R Li 80% 82% Scheme
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13.5 1,4-Addition of Organomanganes
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BuM BuMgCl BuMnCl BuMgCl BuCu BuCu
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13.6 Transition-Metal-Catalyzed Cro
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13.6 Transition-Metal-Catalyzed Cro
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I Cl Scheme 13.56 MeO MnCl (1.2 equ
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13.7 Manganese-Mediated Cross-coupl
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13 C. Boucley, G. Cahiez, unpublish
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570 14 Polyfunctional Electrophilic
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572 14 Polyfunctional Electrophilic
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η5 η6 η4 η7 574 14 Polyfunction
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576 14 Polyfunctional Electrophilic
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578 14 Polyfunctional Electrophilic
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580 14 Polyfunctional Electrophilic
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582 14 Polyfunctional Electrophilic
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584 14 Polyfunctional Electrophilic
- Page 598 and 599:
586 14 Polyfunctional Electrophilic
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588 14 Polyfunctional Electrophilic
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590 14 Polyfunctional Electrophilic
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592 14 Polyfunctional Electrophilic
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51 594 CO 2Me + Fe(CO)3 CO2Me 14 Po
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596 14 Polyfunctional Electrophilic
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598 14 Polyfunctional Electrophilic
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Table 14.1 Examples of synthetic ap
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602 Entry Target molecule Disconnec
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Entry Target molecule Disconnection
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Entry Target molecule Disconnection
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Entry Target molecule Disconnection
- Page 622 and 623:
Target molecule Disconnections Mult
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612 14 Polyfunctional Electrophilic
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614 14 Polyfunctional Electrophilic
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616 14 Polyfunctional Electrophilic
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618 14 Polyfunctional Electrophilic
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620 14 Polyfunctional Electrophilic
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622 14 Polyfunctional Electrophilic
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624 14 Polyfunctional Electrophilic
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626 14 Polyfunctional Electrophilic
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15 Polyfunctional Zinc, Cobalt and
- Page 642 and 643:
Trifluoromethylzinc compounds prepa
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15.3 Electrochemical Synthesis and
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15.3.2 Carbon±Carbon Bond Formatio
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Cl Cl NC + MeO2C 1eq 2eq e, CoX 2 c
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1eq Br FG + R 2eq OAc e, CoX 2 cat
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Cl O + O e, FeBr 2(Bpy) n DMF, Fe a
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15.4 Electrosynthesis of Compounds
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15.4 Electrosynthesis of Compounds
- Page 658 and 659:
FG CuCN/LiCl ZnBr 0ºC CuZnBrCN 15.
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15.4 Electrosynthesis of Compounds
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15.5 General Conclusion (industrial
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17 Durandetti, M.; Devaud, M.; Peri
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I2 Index b-alkoxyalkylidenemalonic,
- Page 668 and 669:
I4 Index boronic ester 47 4-boronyl
- Page 670 and 671:
I6 Index cyclohexadiene 415 cyclohe
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I8 Index fluoroalkenylstannane 206
- Page 674 and 675:
I10 Index iron-catalyzed carbolithi
- Page 676 and 677:
I12 Index nickel-catalyzed carbozin
- Page 678 and 679:
I14 Index psicosecarbene complexes
- Page 680 and 681:
I16 Index Suzuki-Miyaura reaction a