k<strong>in</strong> Trans. 1 1992, 1393; b) M. Sato, H. Ogasawara, K. Oi, T. Kato, Chem. Pharm. Bull. 1983, 31, 1896. 113 V. A. Vu, L. BØrillon, P. Knochel, Tetrahedron Lett. 2001, 42, 6847. 114 J. Thibonnet, V. A. Vu, L. BØrillon, P. Knochel, Tetrahedron, 2002, 58, 4787. 115 R. H. Blaauw, J. C. J. Benn<strong>in</strong>gsh<strong>of</strong>, A. E. Van G<strong>in</strong>kel, J. H. van Maarseveen, H. Hiemstra, J. Chem. Soc., Perk<strong>in</strong> Trans. 1, 2001, 2250. 116 J.-F. BriØre, R. H. Blaauw, J. C. J. Benn<strong>in</strong>gsh<strong>of</strong>, A. E. van G<strong>in</strong>kel, J. H. van Maarseveen, H. Hiemstra, Eur. J. Org. Chem. 2001, 12, 2371. 117 J. Thibonnet, P. Knochel, Tetrahedron Lett. 2000, 41, 3319. 118 a) N. Krause, Tetrahedron Lett. 1989, 30, 5219; b) J. W. J. Kennedy, D. G. Hall, J. Am. Chem. Soc. 2002, 124, 898. 119 F. F. Flem<strong>in</strong>g, V. Gudipati, O. W. Steward, Org. Lett. 2002, 4, 659. 120 P. J. Colson, L. S. Hegedus, J. Org. Chem. 1993, 58, 5918. 121 V. A. Vu, I. Marek, P. Knochel, Synthesis 2003, 1797. 122 a) Satoh, K. Takano, H. Ota, H. Someya, K. Matsuda, M. Koyama, Tetrahedron 1998, 54, 5557; b) T. Satoh, T. Sakamoto, M. Watanabe, K. Takano, Chem. Pharm. Bull. 2003, 51, 966; c) T. Satoh, A. Kondo, J. Musashi, Tetrahedron 2004, 60, 5453; d) T. SAtoh, T. Kurihara, K. Fujita, Tetrahedron 2001, 57, 5369; e) T. Satoh, S. Saito, Tetrahedron Lett. 2004, 45, 347. 123 F. F. Flem<strong>in</strong>g, Z. Zhang, Q. Wang, O. W. Steward, Org. Lett., 2002, 4, 2493. 124 F. F. Flem<strong>in</strong>g, Z. Zhang, Q. Wang, O. W. Steward, J. Org. Chem. 2003, 68, 7646. 125 A. Inoue, H. Sh<strong>in</strong>okubo, K. Oshima, Org. Lett. 2000, 2, 651. 126 V. A. Vu, I. Marek, K. Polborn, P. Knochel, Angew. Chem. 2002, 114,361; Angew. Chem. Int. Ed. Engl. 2002, 41, 351. 127 a) C. Hamdouchi, C. Topolski, M. Goedken, H. M. Walborsky, J. Org. Chem. 1993, 58, 3148; b) G. Boche, D. R. Schneider, Tetrahedron Lett. 1978, 19, 2327; c) G. Boche, D. R. Schneider, H. W<strong>in</strong>termayr, J. Am. Chem. Soc. 1980, 102, 5697. References and Notes 169 128 A. de Meijere, S. I. Kozhushkov, Chem. Rev. 2000, 100, 93. 129 T. Tsuji, T. Nakamura, H. Yorimitsu, H. Sh<strong>in</strong>okubo, K. Oshima, Tetrahedron 2004, 60, 973. 130 a) F. F. Flem<strong>in</strong>g, B. C. Shook, Tetrahedron 2002, 58, 1; b) S. Arseniyadis, K. S. Kyler, D. S. Watt, Org. React. 1984, 31,1. 131 F. F. Flem<strong>in</strong>g, Z. Zhang, P. Knochel, Org. Lett. 2004, 6, 501±503. 132 H. Hart, T. Ghosh, Tetrahedron Lett. 1988, 29, 881. 133 S. Avolio, C. Malan, I. Marek, P. Knochel, Synlett 1999, 1820. 134 a) V. Schulze, M. Broenstrup, V. P. W. Boehm, P. Schwerdtfeger, M. Schimeczek, R. W. H<strong>of</strong>fmann, Angew. Chem. 1998, 110, 869; Angew. Chem. Int. Ed. 1998, 37, 824; b) V. Schulze, R. W. H<strong>of</strong>fmann, Chem. Eur. J. 1999, 5, 337; R. W. H<strong>of</strong>fmann, Chem. Soc. Rev. 2003, 32, 225; c) R. W. H<strong>of</strong>fmann, P. G. Nell, Angew. Chem. 1999, 111, 354; Angew. Chem. Int. Ed. Engl. 1999, 38, 338. 135 N. Millot, C. Piazza, S. Avolio, P. Knochel, Synthesis 2000, 941. 136 F. Dehmel, M. Abarbri, P. Knochel, Synlett 2000, 345. 137 N. Gommermann, C. Korad<strong>in</strong>, P. Knochel, Synthesis 2002, 2143. 138 Pharmaceutical Substances. Syntheses. Patents. <strong>Applications</strong>; A. Kleemann, J. Engel, B. Kutshcer, D. Reichert, Eds., Thieme, Stuttgart, 1999. 139 R. Pandya, T. Murashima, L. Tedeschi, A. G. M. Barrett, J. Org. Chem. 2003, 68, 8274±8276. 140 a) M. T. Reetz, A. K<strong>in</strong>dler, J. Chem. Soc. Chem. Commun. 1994, 2509; b) E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1984, 106, 3368; c) E. J. Corey, N. W. Boaz, Tetrahedron Lett. 1985, 26, 6019; d) A. Alexakis, J. Berlan, Y. Besace, Tetrahedron Lett. 1986, 27, 1047. 141 G. Varchi, A. Ricci, G. Cahiez, P. Knochel, Tetrahedron 2000, 56, 2727. 142 a) K. C. Nicolaou, M. Takayanagi, N. F. Ja<strong>in</strong>, S. Natarajan, A. E. Koumbis, T. Bando, J. M. Ramanjulu, Angew. Chem. 1998, 110, 2881; Angew. Chem. Int. Ed. Engl. 1998, 37, 2717; b) K. C. Nicolaou, A. E. Koumbis,
170 4 Polyfunctional Magnesium <strong>Organometallics</strong> for Organic Synthesis M. Takayanagi, S. Natarajan, N. F. Ja<strong>in</strong>, T. Bando, H. Li, R. Hughes, Chem. Eur. J. 1999, 5, 2622. 143 a) A. Casar<strong>in</strong>i, P. Dembech, D. Lazzari, E. Mar<strong>in</strong>i, G. Reg<strong>in</strong>ato, A. Ricci, G. Seconi, J. Org. Chem. 1993, 58, 5620; b) A. Alberti, F. Cane, P. Dembech, D. Lazzari, A. Ricci, G. Seconi, J. Org. Chem. 1996, 61, 1677; c) F. I. Knight, J. M. Brown, D. Lazzari, A. Ricci, A. J. Blacker, Tetrahedron 1997, 53, 11411; d) P. Dembach, G. Seconi, A. Ricci, Chem. Eur. J. 2000, 6, 1281 144 for some general reviews on electrophilic am<strong>in</strong>ations <strong>of</strong> organometallic reagents, see: a) E. Erdik, M. Ay, Chem. Rev. 1989, 89, 1947; b) G. Boche, <strong>in</strong> Houben-Weyl, Methods <strong>of</strong> Organic Chemistry; G. Helmchen, R. W. H<strong>of</strong>fmann, J. Mulzer, E. Schaumann Eds., Thieme, Stuttgart, 1995. 145 a) F. Terrier, Nucleophilic Aromatic Displacement: The Influence <strong>of</strong> the Nitro Group, VCH, New York, 1991; b) J. F. Bunnett, E. W. Garbisch, K. M. Pruitt, J. Am. Chem. Soc. 1957, 79, 385. 146 a) N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5533; b) S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 6653; c) S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 11684; d) S. L. Buchwald, Org. Lett. 2002, 4, 2885. 147 a) J. P. Wolfe, S. Wagaw, J.-F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998, 31, 805; b) J. F. Hartwig, Angew. Chem. 1998, 110, 2154; Angew. Chem. Int. Ed. Engl. 1998, 37, 2046; c) L. M. Alcazar-Roman, J. F. Hartwig, A. L. Rhe<strong>in</strong>gold, L. M. Liable-Sands, I. A. Guzei, J. Am. Chem. Soc. 2000, 122, 4618; d) J. F. Hartwig <strong>in</strong> <strong>Handbook</strong> <strong>of</strong> Organopalladium Chemistry for Organic Synthesis, Vol. 1, (Eds. E.-I. Negishi, A. de Meijere), John Wiley & Sons, New York, pp. 1051; e) A. R. Muci, S. L. Buchwald, Top. Curr. Chem. 2002, 219, 131. 148 U. K. S<strong>in</strong>gh, E. R. Strieter, D. G. Blackmond, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 14104. 149 for an excellent recent review, see: S. V. Ley, A. W. Thomas, Angew. Chem. 2004, 116, 1061; Angew. Chem. Int. Ed. 2003, 42, 5400. 150 a) J. C. Antilla, S. L. Buchwald, Org. Lett. 2001, 3, 2077; b) J. P. Collman, M. Zhong, Org. Lett. 2000, 2, 1233; c) P. Y. S. Lam, G. V<strong>in</strong>cent, D. Bonne, C. G. Clark, Tetrahedron Lett. 2003, 44, 4927; d) P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600. e) J. Zanon, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 2890; f) F. Y. Kwong, S. L. Buchwald, Org. Lett. 2003, 5, 793; g) D. Zim, S. L. Buchwald, Org. Lett. 2003, 5, 2413. 151 a) B. H. Lipshutz, H. Ueda, Angew. Chem. 2000, 112, 4666; Angew. Chem. Int. Ed. 2000, 39, 4492; b) C. Desmartes, R. Schneider, Y. Fort, Tetrahedron Lett. 2001, 42, 247. 152 D. Seeebach, Angew. Chem. 1979, 91, 259; Angew. Chem. Int. Ed. Engl. 1979, 18, 239. 153 a) H. Wieland, Chem. Ber. 1903, 36, 2315; b) T. Sever<strong>in</strong>, R. Schmitz, Chem. Ber. 1963, 96, 3081; c) T. Sever<strong>in</strong>, M. Adam, Chem. Ber. 1964, 97, 186. 154 H. Gilman, R. McCracken, J. Am. Chem. Soc. 1927, 49, 1052. 155 a) G. Bartoli, M. Bosco, G. Cantagalli, R. Dalpozzo, F. Cim<strong>in</strong>ale, J. Chem. Soc., Perk<strong>in</strong> Trans. 2 1985, 773; b) G. Bartoli, M. Bosco, R. Dalpozzo, G. Calmieri, E. Marcantoni, J. Chem. Soc. Perk<strong>in</strong> Trans. 1, 1991, 2757. 156 a) G. Bartoli, Acc. Chem. Res. 1984, 17, 109; b) M. Bosco, R. Dalpozzo, G. Batoli, G. Calmieri, M. Petr<strong>in</strong>i, J. Chem. Soc., Perk<strong>in</strong> Trans. 2 1991, 657. 157 A. Ono, H. Sasaki, F. Yag<strong>in</strong>uma, Chem. Ind. (London) 1983, 480. 158 a) I. Sapountzis, P. Knochel, J. Am. Chem. Soc. 2002, 124, 9390; b) I. Sapountzis, P. Knochel, manuscript <strong>in</strong> preparation; c) I. Sapountzis, N. Gommermann, P. Knochel, manuscript <strong>in</strong> preparation. 159 a) B. H. Yang, S. L. Buchwald, J. Organomet. Chem. 1999, 576, 125; b) J. P. Wolfe, S. Wagan, J.-F. Marcoux, S. L. Buchwald, Acc. Chem. Res. 1998,
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Organometallics. Paul Knochel Copyr
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Handbook of Functionalized Organome
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Contents Preface XV List of Authors
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Contents 3.3.9 Oxidation of Functio
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6.3.1 Nucleophilic Addition onto Ca
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9.2.3 Preparation of Functionalized
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13.6.4 Nickel-Catalyzed Cross-coupl
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Preface Since the pioneering work o
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XVIII List of Authors Corinne Gosmi
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1 Introduction Paul Knochel and Fel
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umorganic is directly generated in
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Et H 21 Et AlBu 2 + CO 2Et Cu(CN)Mg
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8 2 Polyfunctional Lithium Organome
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10 2 Polyfunctional Lithium Organom
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R R 12 2 Polyfunctional Lithium Org
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MeO MeO R 14 2 Polyfunctional Lithi
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N 16 2 Polyfunctional Lithium Organ
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18 2 Polyfunctional Lithium Organom
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Li LiO 20 2 Polyfunctional Lithium
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Li 22 2 Polyfunctional Lithium Orga
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24 2 Polyfunctional Lithium Organom
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26 Ph O Ni-Pr 2 2 Polyfunctional Li
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28 Li 2 Polyfunctional Lithium Orga
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30 2 Polyfunctional Lithium Organom
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Li 32 203 2 Polyfunctional Lithium
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34 2 Polyfunctional Lithium Organom
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36 Br 2 Polyfunctional Lithium Orga
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38 2 Polyfunctional Lithium Organom
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40 2 Polyfunctional Lithium Organom
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42 2 Polyfunctional Lithium Organom
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3 Functionalized Organoborane Deriv
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Br SSiMe 2tBu 4 3.2 Preparation and
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B O O 3.2 Preparation and Reaction
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3.2 Preparation and Reaction of Fun
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3.2 Preparation and Reaction of Fun
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Ar H Ar = O HB O CF 3 CF 3 3.2 Prep
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3.2 Preparation and Reaction of Fun
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X X Cl Cl TfO Cl 3.2 Preparation an
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HO HO Br OH O X N N O N 3.2 Prepara
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MOMO MOMO I CbzN O 3.2 Preparation
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3.2 Preparation and Reaction of Fun
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(HO) 3B O NMe 3 N N O Br 3.2 Prepar
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H H O O N H N H O OEt O O OEt O 3.2
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t BuO2C O N H 3.2 Preparation and R
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3.2 Preparation and Reaction of Fun
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3.2 Preparation and Reaction of Fun
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3.2 Preparation and Reaction of Fun
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R H2O R R B(OH) 2 B(OH) 2 3.3 Prepa
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3.3 Preparation and Reactions of Fu
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R 124 BF 3K Br 3.3 Preparation and
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B O O I OR O OR O O O O O OR 3.3 Pr
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S N O B O I O 133 3.4 Preparation a
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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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- Page 188 and 189: 31, 805; J. F. Hartwig, Angew. Chem
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- Page 192 and 193: stereocontrol [5]. Similar chiral c
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- Page 218 and 219: 716. (c)I. E. Markó, J.-M. Planche
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- Page 222 and 223: phine ligand or Pd II (PPh 3) 2Cl 2
- Page 224 and 225: Bu 3 Sn Scheme 6.4 n-Pent + Me I O
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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
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Br CO 2Et I CO 2Et CO 2Et Np 2CuLi
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9.2 Preparation of Functionalized O
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Pent I O O Pent I CO 2Et O Br Pent
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Ph Ph N OMe 1) n-BuLi 2) alkynylcop
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9.3 Applications of Functionalized
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PrCu·MgBr 2·SMe 2 Pr Me H Pr H HO
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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
- Page 452 and 453:
O 438 O Br 10 Functional Organonick
- Page 454 and 455:
440 10 Functional Organonickel Reag
- Page 456 and 457:
Cl 442 CN 10 Functional Organonicke
- Page 458 and 459:
444 10 Functional Organonickel Reag
- Page 460 and 461:
446 10 Functional Organonickel Reag
- Page 462 and 463:
448 10 Functional Organonickel Reag
- Page 464 and 465:
11 Polyfunctional Metal Carbenes fo
- Page 466 and 467:
11.2 Chromium-Templated Cycloadditi
- Page 468 and 469:
11.2 Chromium-Templated Cycloadditi
- Page 470 and 471:
(CO) 5Cr O Ph 15 1) t Bu t BuOMe, 5
- Page 472 and 473:
O MeO O O O O MeO O OMe Cr(CO) 5 Me
- Page 474 and 475:
11.2.3 Cyclization of Chromium Olig
- Page 476 and 477:
(CO)5Cr OR * O S + OMe 11.2 Chromiu
- Page 478 and 479:
[2+2+1] R 1 R 1 OH (CO) 5Cr R 2 (CO
- Page 480 and 481:
11.3 Reactions of Higher Nuclearity
- Page 482 and 483:
Br O X Br O R 2 R 2 O 85: X = Si-tB
- Page 484 and 485:
11.3 Reactions of Higher Nuclearity
- Page 486 and 487:
11.4 Metathesis Reactions Catalyzed
- Page 488 and 489:
R 2 R 1 O R O 3 O 11.4 Metathesis R
- Page 490 and 491:
i Pr i Pr i Pr Me Me (R)-160 Ph O O
- Page 492 and 493:
11.5 Transmetallation The dimerizat
- Page 494 and 495:
11.6 Metal Carbenes in Peptide Chem
- Page 496 and 497:
11.7 Stereoselective Syntheses with
- Page 498 and 499:
11.7 Stereoselective Syntheses with
- Page 500 and 501:
11.7 Stereoselective Syntheses with
- Page 502 and 503:
11.7 Stereoselective Syntheses with
- Page 504 and 505:
11.7 Stereoselective Syntheses with
- Page 506 and 507:
O O O O 100% H 2N O O O O O 311a Cr
- Page 508 and 509:
11.8 Sugar Metal Carbenes as Organo
- Page 510 and 511:
References zation reactions that al
- Page 512 and 513:
35 (a) C.A. Merlic, Y. You, D.M. Mc
- Page 514 and 515:
D. R. Cefalo, P. J. Bonitatebus Jr.
- Page 516 and 517:
12 Functionalized Organozirconium a
- Page 518 and 519:
12.2 Functionalized Organozirconoce
- Page 520 and 521:
Ph O (H)ZrCp Ph O 2Cl Ph O O O 92 %
- Page 522 and 523:
12.2 Functionalized Organozirconoce
- Page 524 and 525:
i-PrO O OBu-t O H N Scheme 12.15 H
- Page 526 and 527:
BnO Scheme 12.19 O BnO + 27 28 Cp 2
- Page 528 and 529:
12.2 Functionalized Organozirconoce
- Page 530 and 531:
R 1 O O O R R1 R 2 Scheme 12.28 R P
- Page 532 and 533:
12.2 Functionalized Organozirconoce
- Page 534 and 535:
12.3 Functionalized Organotitanium
- Page 536 and 537:
12.3 Functionalized Organotitanium
- Page 538 and 539:
t-BuOOC Scheme 12.44 O CH 3 7.5 mol
- Page 540 and 541:
12.3 Functionalized Organotitanium
- Page 542 and 543:
H 13C 6 O R Scheme 12.52 SiMe 3 O T
- Page 544 and 545:
12.3 Functionalized Organotitanium
- Page 546 and 547:
O O OEt 87 Scheme 12.59 Scheme 12.6
- Page 548 and 549:
12.3 Functionalized Organotitanium
- Page 550 and 551:
12.3 Functionalized Organotitanium
- Page 552 and 553:
40 A. M. Sun, X. Huang, Heteroatom
- Page 554 and 555:
13 Manganese Organometallics for th
- Page 556 and 557:
13.2.2 Preparation of Organomangane
- Page 558 and 559:
13.3 1,2-Addition to Aldehydes and
- Page 560 and 561:
13.3.2 Manganese-Mediated Barbier-
- Page 562 and 563:
HeptMnX + HeptMnX + Scheme 13.17 Cl
- Page 564 and 565:
13.4 Preparation of Ketones by Acyl
- Page 566 and 567:
Me 3Si Cl ( ) 3 R Li 80% 82% Scheme
- Page 568 and 569:
13.5 1,4-Addition of Organomanganes
- Page 570 and 571:
BuM BuMgCl BuMnCl BuMgCl BuCu BuCu
- Page 572 and 573:
13.6 Transition-Metal-Catalyzed Cro
- Page 574 and 575:
13.6 Transition-Metal-Catalyzed Cro
- Page 576 and 577:
I Cl Scheme 13.56 MeO MnCl (1.2 equ
- Page 578 and 579:
13.7 Manganese-Mediated Cross-coupl
- Page 580 and 581:
13 C. Boucley, G. Cahiez, unpublish
- Page 582 and 583:
570 14 Polyfunctional Electrophilic
- Page 584 and 585:
572 14 Polyfunctional Electrophilic
- Page 586 and 587:
η5 η6 η4 η7 574 14 Polyfunction
- Page 588 and 589:
576 14 Polyfunctional Electrophilic
- Page 590 and 591:
578 14 Polyfunctional Electrophilic
- Page 592 and 593:
580 14 Polyfunctional Electrophilic
- Page 594 and 595:
582 14 Polyfunctional Electrophilic
- Page 596 and 597:
584 14 Polyfunctional Electrophilic
- Page 598 and 599:
586 14 Polyfunctional Electrophilic
- Page 600 and 601:
588 14 Polyfunctional Electrophilic
- Page 602 and 603:
590 14 Polyfunctional Electrophilic
- Page 604 and 605:
592 14 Polyfunctional Electrophilic
- Page 606 and 607:
51 594 CO 2Me + Fe(CO)3 CO2Me 14 Po
- Page 608 and 609:
596 14 Polyfunctional Electrophilic
- Page 610 and 611:
598 14 Polyfunctional Electrophilic
- Page 612 and 613:
Table 14.1 Examples of synthetic ap
- Page 614 and 615:
602 Entry Target molecule Disconnec
- Page 616 and 617:
Entry Target molecule Disconnection
- Page 618 and 619:
Entry Target molecule Disconnection
- Page 620 and 621:
Entry Target molecule Disconnection
- Page 622 and 623:
Target molecule Disconnections Mult
- Page 624 and 625:
612 14 Polyfunctional Electrophilic
- Page 626 and 627:
614 14 Polyfunctional Electrophilic
- Page 628 and 629:
616 14 Polyfunctional Electrophilic
- Page 630 and 631:
618 14 Polyfunctional Electrophilic
- Page 632 and 633:
620 14 Polyfunctional Electrophilic
- Page 634 and 635:
622 14 Polyfunctional Electrophilic
- Page 636 and 637:
624 14 Polyfunctional Electrophilic
- Page 638 and 639:
626 14 Polyfunctional Electrophilic
- Page 640 and 641:
15 Polyfunctional Zinc, Cobalt and
- Page 642 and 643:
Trifluoromethylzinc compounds prepa
- Page 644 and 645:
15.3 Electrochemical Synthesis and
- Page 646 and 647:
15.3.2 Carbon±Carbon Bond Formatio
- Page 648 and 649:
Cl Cl NC + MeO2C 1eq 2eq e, CoX 2 c
- Page 650 and 651:
1eq Br FG + R 2eq OAc e, CoX 2 cat
- Page 652 and 653:
Cl O + O e, FeBr 2(Bpy) n DMF, Fe a
- Page 654 and 655:
15.4 Electrosynthesis of Compounds
- Page 656 and 657:
15.4 Electrosynthesis of Compounds
- Page 658 and 659:
FG CuCN/LiCl ZnBr 0ºC CuZnBrCN 15.
- Page 660 and 661:
15.4 Electrosynthesis of Compounds
- Page 662 and 663:
15.5 General Conclusion (industrial
- Page 664 and 665:
17 Durandetti, M.; Devaud, M.; Peri
- Page 666 and 667:
I2 Index b-alkoxyalkylidenemalonic,
- Page 668 and 669:
I4 Index boronic ester 47 4-boronyl
- Page 670 and 671:
I6 Index cyclohexadiene 415 cyclohe
- Page 672 and 673:
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