A simple and efficient copper-catalyzed procedure for the hydrosilylation of hindered and functionalized ketones

被引：162

作者：

Díez-González, S ^{[1
]}

Kaur, H ^{[1
]}

Zinn, FK ^{[1
]}

Stevens, ED ^{[1
]}

Nolan, SP ^{[1
]}

机构：

[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 12期

关键词：

D O I：

10.1021/jo050397v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The catalytic hydrosilylation of highly hindered and functionalized ketones is described. The combination of inexpensive catalyst precursors, CuCl and NHC-HX (NHC = N-heterocyclic carbene), leads to a highly efficient reduction mediator for the preparation of silyl ethers from unfunctionalized and functionalized alkyl, cyclic, bicyclic, aromatic, and heteroaromatic ketones. A series of catalyst precursors have been structurally characterized and a catalyst-structure activity relationship is discussed.

引用

页码：4784 / 4796

页数：13

共 72 条

[41] HYDRIDE-MEDIATED HOMOGENEOUS CATALYSIS - CATALYTIC REDUCTION OF ALPHA,BETA-UNSATURATED KETONES USING [(PH3P)CUH]6 AND H2 [J].

MAHONEY, WS ;

STRYKER, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8818-8823

[42] Synthesis, structure, and alkyne reactivity of a dimeric (carbene)copper(I) hydride [J].

Mankad, NP ;

Laitar, DS ;

Sadighi, JP .

ORGANOMETALLICS, 2004, 23 (14) :3369-3371

[43] Synthesis, structure, and CO2 reactivity of a two-coordinate (carbene)copper(I) methyl complex [J].

Mankad, NP ;

Gray, TG ;

Laitar, DS ;

Sadighi, JP .

ORGANOMETALLICS, 2004, 23 (06) :1191-1193

[44] Synthesis of β-alkyl cyclopentanones in high enantiomeric excess via copper-catalyzed asymmetric conjugate reduction [J].

Moritani, Y ;

Appella, DH ;

Jurkauskas, V ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (28) :6797-6798

[45] A general method for the Suzuki-Miyaura cross-coupling of sterically hindered aryl chlorides: Synthesis of di- and tri-ortho-substituted biaryls in 2-propanol at room temperature [J].

Navarro, O ;

Kelly, RA ;

Nolan, SP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (52) :16194-16195

[46] CHIRAL OXAZOLINYLFERROCENE-PHOSPHINE HYBRID LIGAND FOR THE ASYMMETRIC HYDROSILYLATION OF KETONES [J].

NISHIBAYASHI, Y ;

SEGAWA, K ;

OHE, K ;

UEMURA, S .

ORGANOMETALLICS, 1995, 14 (12) :5486-5487

[47] Ruthenium-catalyzed asymmetric hydrosilylation of ketones and imine [J].

Nishibayashi, Y ;

Takei, I ;

Uemura, S ;

Hidai, M .

ORGANOMETALLICS, 1998, 17 (16) :3420-3422

[48] CHIRAL AND C-2-SYMMETRICAL BIS(OXAZOLINYLPYRIDINE)RHODIUM(III) COMPLEXES - EFFECTIVE CATALYSTS FOR ASYMMETRIC HYDROSILYLATION OF KETONES [J].

NISHIYAMA, H ;

SAKAGUCHI, H ;

NAKAMURA, T ;

HORIHATA, M ;

KONDO, M ;

ITOH, K .

ORGANOMETALLICS, 1989, 8 (03) :846-848

[49] General asymmetric hydrogenation of hetero-aromatic ketones [J].

Ohkuma, T ;

Koizumi, M ;

Yoshida, M ;

Noyori, R .

ORGANIC LETTERS, 2000, 2 (12) :1749-1751

[50]

Ojima I, 1998, CHEM FUNCT, V2, P1687, DOI 10.1002/0470857250.ch29

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