Highly selective coupling of alkenes and aldehydes catalyzed by [Ni(NHC){P(OPh)3}]:: Synergy between a strong σ donor and a strong π acceptor

被引：103

作者：

Ho, Chun-Yu ^{[1
]}

Jamison, Timothy F. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 05期

关键词：

D O I：

10.1002/anie.200603907

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Give and take: Both a strong electron donor (1) and a strong electron acceptor (P(OPh)3) are necessary for a highly selective, nickel-catalyzed coupling reaction between alkenes, aldehydes, and silyl triflates (see scheme; cod = cycloocta-1,5-diene, Tf=trifluoromethanesulfonyl). This synergistic effect may also be useful in other transformations catalyzed by NHC-metal complexes (NHC = N-heterocyclic carbene). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

收藏

页码：782 / 785

页数：4

相关论文

共 45 条

[1] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[2] A mild and efficient catalytic alkylative monofunctionalization of cyclic anhydrides [J].

Bercot, EA ;

Rovis, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (02) :174-175

[3]

Blom R., 2001, ORGANOMETALLIC CATAL, DOI DOI 10.1007/978-3-642-59465-6

[4]

Clement N. D., 2004, ANGEW CHEM, V116, P1297

[5]

Clement N. D., 2004, ANGEW CHEM, V116, P3933

[6] Transition-metal-catalyzed reactions involving imidazolium salt/N-heterocyclic carbene couples as substrates [J].

Clement, ND ;

Cavell, KJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3845-3847

[7] Oxidative addition of imidazolium salts to Ni0 and Pd0:: Synthesis and structural characterization of unusually stable metal-hydride complexes [J].

Clement, ND ;

Cavell, KJ ;

Jones, C ;

Elsevier, CJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (10) :1277-1279

[8] NHC ligands versus cyclopentadienyls and phosphines as spectator ligands in organometallic catalysis [J].

Crabtree, RH .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) :5451-5457

[9] Stability and reactivity of N-heterocyclic carbene complexes [J].

Crudden, CM ;

Allen, DP .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2247-2273

[10] Chiral Lewis acid catalyzed ene-reactions [J].

Dias, LC .

CURRENT ORGANIC CHEMISTRY, 2000, 4 (03) :305-342

← 1 2 3 4 5 →