Efficient and stereoselective cross-coupling with highly substituted alkenylsilanols

被引：27

作者：

Denmark, SE ^{[1
]}

Pan, WT ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2002年 / 653卷 / 1-2期

基金：

美国国家科学基金会;

关键词：

cross-coupling; alkenylsilanols; palladium catalysis;

D O I：

10.1016/S0022-328X(02)01268-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Highly substituted alkenylsilanols (1), readily prepared from commercially available simple starting materials, are efficiently-coupled with aryl or alkenyl halides in the presence of tetrabutylammonium fluoride (TBAF) and a palladium(0) catalyst. Yields are generally high and the reactions are highly stereoselective and compatible with a wide range of functional groups. (C) 2002 Elsevier Science B.V. All rights reserved.

引用

页码：98 / 104

页数：7

共 41 条

[1] Phenyl β-methoxyacrylates:: A new antimalarial pharmacophore [J].

Alzeer, J ;

Chollet, J ;

Heinze-Krauss, I ;

Hubschwerlen, C ;

Matile, H ;

Ridley, RG .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (04) :560-568

[2]

BARCZA S, 1987, SILICON CHEM

[3] Total synthesis of the cholesterol biosynthesis inhibitor 1233A via a (π-allyl)tricarbonyliron lactone complex [J].

Bates, RW ;

Fernández-Megía, E ;

Ley, SV ;

Rück-Braun, K ;

Tilbrook, DMG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (14) :1917-1925

[4] PALLADIUM-CATALYZED VINYLATION OF TERTIARY ALLYLIC ALCOHOLS - A NEW PROTOCOL FOR THE SYNTHESIS OF ISOPRENOID ALDEHYDES [J].

BIENAYME, H ;

YEZEGUELIAN, C .

TETRAHEDRON, 1994, 50 (11) :3389-3396

[5]

Cahard D, 1998, SYNLETT, P1399

[6] OBSERVATIONS REGARDING THE REGIOCHEMICAL AND STEREOCHEMICAL COURSE OF THE CYCLIZATION OF COMPLEX 5-HEXENYL RADICALS - AN APPROACH TO PERHYDRONAPHTHALENES [J].

CHUANG, CP ;

GALLUCCI, JC ;

HART, DJ ;

HOFFMAN, C .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14) :3218-3226

[7] Highly stereospecific, palladium-catalyzed cross-coupling of alkenylsilanols [J].

Denmark, SE ;

Wehrli, D .

ORGANIC LETTERS, 2000, 2 (04) :565-568

[8] Intramolecular hydrosilylation and silicon-assisted cross-coupling: An efficient route to trisubstituted homoallylic alcohols [J].

Denmark, SE ;

Pan, WT .

ORGANIC LETTERS, 2001, 3 (01) :61-64

[9] (E)-3-(TRIMETHYLSILYL)-2-PROPEN-1-OL - AN IMPROVED PREPARATION [J].

DENMARK, SE ;

JONES, TK .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) :4595-4597

[10] Synthesis of unsymmetrical biaryls from arylsilacyclobutanes [J].

Denmark, SE ;

Wu, ZC .

ORGANIC LETTERS, 1999, 1 (09) :1495-1498

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