Handbook of Functionalized Organometallics Applications in S

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13 C. Boucley, G. Cahiez, unpublished results 14 M. T. Reetz, H. Haning, S. Stanchev, Tetrahedron 1992, 33, 6963±6966. 15 C. Boucley, G. Cahiez, S. Carini, V. Cere, M. Comes-Franchini, P. Knochel, S. Pollicino, A. Ricci, J. Organomet. Chem. 2001, 223±228. 16 G. Cahiez, P.-Y. Chavant, Tetrahedron Lett. 1989, 30, 7373±7376. 17 S. Bergström, G. Aulin-Erdtman, B. Rolander, E. Steinhagen, S. Östling, Acta Chem. Scand. 1952, 1157. 18 G. Cahiez, P.Y. Chavant, E. MØtais, Tetrahedron Lett. 1992, 33, 5245±5248. 19 T. Matsuura, Bull. Chem. Soc. Jpn. 1957, 30, 430. 20 D S. Ennis, T. L. Gilchrist, Tetrahedron 1990, 46, 2623±2632. 21 a) T. Ueda, Y. Fujita, Chem Ind. 1962, 1618±1619. b) T. R. Bailey, Synthesis 1991, 242±243. 22 Y. Kojima, S. Wakita, N. Kato, Tetrahedron Lett. 1979, 20, 4577±4580. 23 G. Buechi, E. Kovats, P. Enggist, G. Uhde, J. Org. Chem. 1968, 33, 1227±1229. 24 G. Cahiez, Tetrahedron Lett. 1981, 22, 1239±1242. 25 G . Cahiez, E. MØtais, Tetrahedron Lett. 1995, 36, 6449±6452. 26 G. Cahiez, E. MØtais, Tetrahedron Asymm. 1997, 8, 1373±1376. 27 G. Cahiez, J. Rivas-Enterrios, H. Granger-Veyron, Tetrahedron Lett. 1986, 27, 4441±4444. References 567 28 G. Cahiez, J. Rivas-Enterrios, P. ClØry, Tetrahedron Lett. 1988, 29, 3659±3662. 29 G. Cahiez, B. Laboue, P.Tozzolino, Eur. Pat. Appl. EP 374015 FR. Appl. 88/16598, 1988. 30 I. Klement, H. Stadtmüller, P. Knochel, G. Cahiez, Tetrahedron Lett. 1997, 38, 1927±1930. 31 S.-H. Kim, R. D. Rieke, J. Org. Chem. 2000, 65, 2322±2330. 32 G. Cahiez, B. Laboue, Tetrahedron Lett. 1992, 33, 4439±4442. 33 G. Cahiez, M. Alami, Tetrahedron 1985, 45, 4163±4176. 34 G. Cahiez, M. Alami, Tetrahedron Lett. 1986, 27, 569±572. 35 G. Cahiez, S. Marquais, M. Alami, Organic Syntheses 1993, 72, 135. 36 G. Cahiez, M. Alami, Tetrahedron Lett. 1989, 30, 7365±7368. 37 C. Chuit, J. P. Foulon, J. Normant, Tetrahedron 1980, 36, 2305±2310. 38 G. Cahiez, S. Marquais, Synlett 1993,45. 39 G. Cahiez, S. Marquais, Tetrahedron Lett. 1996, 37, 1773±1776. 40 E. Riguet, M. Alami, G. Cahiez, Tetrahedron Lett. 1997, 38, 4397±4400. 41 M. Alami, P. Ramiandrasoa, G. Cahiez, Synlett 1998, 325±327. 42 G. Cahiez, F. Lepifre, P. Ramiandrasoa, Synthesis 1999, 2138±2144. 43 G. Cahiez, D. Luart, F. Lecomte, Org. Lett. 2004, 24, 4395±4398. 44 E. Riguet, I. Klement, C. Kishan Reddy, G. Cahiez, P. Knochel, Tetrahedron Lett. 1996, 37, 5865±5868.
14 Polyfunctional Electrophilic Multihapto-Organometallics for Organic Synthesis G. Richard Stephenson The attachment of a transition metal to an unsaturated hydrocarbon ligand transforms the reactivity properties of the ligand. Whereas the classic chemistry of alkenes and arenes is that of electrophilic addition and substitution reactions, the classic reactivity of multihapto-complexes is their reactions with nucleophiles. Such complexes need not be cationic to be good electrophiles, but it helps, and not surprisingly, the most powerful electrophilic multihapto-complexes have positive charge stabilized by the metal. 14.1 Introduction to Multihapto-Complexes and Discussion of Nomenclature The intention of this chapter is to set out the patterns of reactivity of electrophilic multihapto-complexes with nucleophiles, with particular regard to the effects of substituents on the haptyl portion of the ligand. Addition of a nucleophile to an electrophilic multihapto-complex reduces hapticity by 1. Thus a cationic g n electrophile { [g n ] + } is converted into a neutral product { [g n±1 ] } when, for example, a nucleophile adds at one end of the p-system, as illustrated in Fig. 14.1. If the electrophilic complex is neutral, then the corresponding reaction is: { [g n ]}® {[g n±1 ] ± }, and the product is an anion. When the nucleophile adds at an internal position (see Section 14.3.8), the outcome is essentially the same, but it is the sum of the hapticities in the product that adds to a value that is one less than n'intheg n starting material. There are in general two classes of electrophilic multihapto-complexes: those with cyclic p-systems, referred to as ªclosedº complexes [1], and those in which the p-system is ªopenº (e.g., linear). To further complicate the situation, the haptyl section of an open ligand can also be branched, and exocyclic extensions can embellish cyclic p-systems. More than one haptyl region can be present in an individual ligand, and several unsaturated ligands can bind to the same metal. Thus a wide range of selectivity issues are encountered: there can be competition between ligands in the same cationic metal complex, there can be competition between haptyl regions attached to the same metal, and there can be competition between the different atoms of most reactive haptyl portion of the complex. Each Organometallics. Paul Knochel Copyright 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim ISBN: 3-527-31131-9 569
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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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Li LiO 20 2 Polyfunctional Lithium
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Li 22 2 Polyfunctional Lithium Orga
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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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Li 32 203 2 Polyfunctional Lithium
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36 Br 2 Polyfunctional Lithium Orga
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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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Ar H Ar = O HB O CF 3 CF 3 3.2 Prep
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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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(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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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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R TrocO S N R 1 O S N 13 12 O 1 160
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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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NC Br Br 4.2Methods of Preparation
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N N Ph I 4.2Methods of Preparation
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Cl MgBr 4.2Methods of Preparation o
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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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4.3 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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Me OTf CO2Et + Me 4.4 Application o
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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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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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Bu S O IZn(CH 2) 4ZnI 94 268 7 Poly
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OAc MeO I EtO 2C 272 CHO S C N 7 Po
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276 O 7 Polyfunctional Zinc Organom
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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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288 Ph N 214 O 7 Polyfunctional Zin
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294 IZn AcO 7 Polyfunctional Zinc O
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O 310 7 Polyfunctional Zinc Organom
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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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348 8 Polyfunctional 1,1-Organodime
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350 O 8 Polyfunctional 1,1-Organodi
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CH 2(ZnI) 2 4 362 8 Polyfunctional
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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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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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O 438 O Br 10 Functional Organonick
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Cl 442 CN 10 Functional Organonicke
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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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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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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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Page 530 and 531: R 1 O O O R R1 R 2 Scheme 12.28 R P
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Page 552 and 553: 40 A. M. Sun, X. Huang, Heteroatom
Page 554 and 555: 13 Manganese Organometallics for th
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Page 570 and 571: BuM BuMgCl BuMnCl BuMgCl BuCu BuCu
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Page 576 and 577: I Cl Scheme 13.56 MeO MnCl (1.2 equ
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Page 586 and 587: η5 η6 η4 η7 574 14 Polyfunction
Page 606 and 607: 51 594 CO 2Me + Fe(CO)3 CO2Me 14 Po
Page 612 and 613: Table 14.1 Examples of synthetic ap
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618 14 Polyfunctional Electrophilic
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15 Polyfunctional Zinc, Cobalt and
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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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FG CuCN/LiCl ZnBr 0ºC CuZnBrCN 15.
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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,
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I4 Index boronic ester 47 4-boronyl
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I6 Index cyclohexadiene 415 cyclohe
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I8 Index fluoroalkenylstannane 206
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I10 Index iron-catalyzed carbolithi
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I12 Index nickel-catalyzed carbozin
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I14 Index psicosecarbene complexes
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I16 Index Suzuki-Miyaura reaction a
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