Vinylation of aryl bromides using an inexpensive vinylpolysiloxane

被引：71

作者：

Denmark, SE ^{[1
]}

Butler, CR ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 01期

关键词：

D O I：

10.1021/ol052517r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and general method for the palladium-catalyzed vinylation of aryl bromides has been developed. The use of tetrabutylammonium fluoride (TBAF) as the activator and an inexpensive and nontoxic vinyl donor, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane (D-4(V), 1), allows for a general and high-yielding preparation of substituted styrenes.

引用

页码：63 / 66

页数：4

共 28 条

[1] ASYMMETRIC HYDROFORMYLATION [J].

AGBOSSOU, F ;

CARPENTIER, JF ;

MORTREAUX, A .

CHEMICAL REVIEWS, 1995, 95 (07) :2485-2506

[2] Palladium catalyzed cross-coupling reaction of Grignard reagents with halobenzoic acids, halophenols and haloanilines [J].

Bumagin, NA ;

Luzikova, EV .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 532 (1-2) :271-273

[3] Regio- and enantiocontrol in the room-temperature hydroboration of vinyl arenes with pinacol borane [J].

Crudden, CM ;

Hleba, YB ;

Chen, AC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9200-9201

[4]

Darses S, 1999, EUR J ORG CHEM, V1999, P1875

[5] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis [J].

Deiters, A ;

Martin, SF .

CHEMICAL REVIEWS, 2004, 104 (05) :2199-2238

[6] Cross-coupling of vinylpolysiloxanes with aryl iodides [J].

Denmark, SE ;

Wang, ZG .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) :372-375

[7]

Denmark SE, 2000, SYNTHESIS-STUTTGART, P999

[8] THE PREPARATION OF SUBSTITUTED STYRENES BY METHODS NOT INVOLVING HYDROCARBON CRACKING [J].

EMERSON, WS .

CHEMICAL REVIEWS, 1949, 45 (02) :347-383

[9] Palladium/imidazolium salt catalyzed coupling of aryl halides with hypervalent organostannates [J].

Grasa, GA ;

Nolan, SP .

ORGANIC LETTERS, 2001, 3 (01) :119-122

[10]

Grubbs R.H., 2003, HDB METATHESIS, V3

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