Palladium-catalyzed cross-coupling reaction using alkenyldimethyl(2-thienyl)silanes

被引：14

作者：

Hosoi, K ^{[1
]}

Nozaki, K ^{[1
]}

Hiyama, T ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan

来源：

PROCEEDINGS OF THE JAPAN ACADEMY SERIES B-PHYSICAL AND BIOLOGICAL SCIENCES | 2002年 / 78卷 / 06期

关键词：

cross-coupling; organosilicon compounds; 2-thienyl group; palladium catalyst;

D O I：

10.2183/pjab.78.154

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Alkenyldimethyl(2-thienyl)silanes underwent the cross-coupling reaction with organic halides mediated by tetrabutylammonium fluoride and a palladium catalyst under extremely mild conditions to afford alkenyl-coupled products in good to excellent yields. Starting front 1,2-bissilylated alkenes, 1,2-disubstituted olefins were also synthesized and successfully applied to the cross-coupling reaction.

引用

页码：154 / 160

页数：7

共 54 条

[1] A CONVENIENT AND NOVEL ROUTE TO BIS(ETA-ALKYNE)PLATINUM(0) AND OTHER PLATINUM(0) COMPLEXES FROM SPEIER HYDROSILYLATION CATALYST H2[PTCL6].XH2O - X-RAY STRUCTURE OF [PT((ETA-CH2=CHSIME2)2O)(P-TERT-BU3)] [J].

CHANDRA, G ;

LO, PY ;

HITCHCOCK, PB ;

LAPPERT, MF .

ORGANOMETALLICS, 1987, 6 (01) :191-192

[2] Pd-catalyzed cross-coupling of alkynylsilanols with iodobenzenes [J].

Chang, S ;

Yang, SH ;

Lee, PH .

TETRAHEDRON LETTERS, 2001, 42 (29) :4833-4835

[3] Intramolecular silicon-assisted cross-coupling reactions:: General synthesis of medium-sized rings containing a 1,3-cis-cis diene unit [J].

Denmark, SE ;

Yang, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (10) :2102-2103

[4] Fluoride-free cross-coupling of organosilanols [J].

Denmark, SE ;

Sweis, RF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (26) :6439-6440

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

Denmark, SE ;

Wehrli, D .

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

[6] Sequential ring-closing metathesis and silicon-assisted cross-coupling reactions: Stereocontrolled synthesis of highly substituted unsaturated alcohols [J].

Denmark, SE ;

Yang, SM .

ORGANIC LETTERS, 2001, 3 (11) :1749-1752

[7] 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

[8] Highly stereoselective hydrocarbation of terminal alkynes via Pt-catalyzed hydrosilylation/Pd-catalyzed cross-coupling reactions [J].

Denmark, SE ;

Wang, ZG .

ORGANIC LETTERS, 2001, 3 (07) :1073-1076

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

Denmark, SE ;

Wu, ZC .

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

[10] Highly stereospecific, cross-coupling reactions of alkenylsilacyclobutanes [J].

Denmark, SE ;

Choi, JY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) :5821-5822

← 1 2 3 4 5 6 →