Initial investigation into the Suzuki-Miyaura vinylation of hindered aryl bromides utilizing potassium vinyltrifluoroborate

被引：11

作者：

Carter, Rhiannon R. ^{[1
]}

Wyatt, Justin K. ^{[1
]}

机构：

[1] Coll Charleston, Dept Chem & Biochem, Charleston, SC 29424 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 34期

基金：

美国国家卫生研究院;

关键词：

Suzuki-Miyaura; potassium vinyltrifluoroborate; styrenes; palladium catalysis; hindered aryl bromides; CROSS-COUPLING REACTIONS; HALIDES; MILD;

D O I：

10.1016/j.tetlet.2006.06.083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An initial study of the Suzuki-Miyaura cross-coupling of potassium vinyltrifluoroborate (2) and hindered aryl bromides is presented. Coupling of benzyl 3,5-bis(benzyloxy)-4-bromobenzoate (1) leads to a mixture of the desired styrene derivative, and the reduced product. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：6091 / 6094

页数：4

共 17 条

[1] Palladium catalyzed cross-coupling reaction of Grignard reagents with halobenzoic acids, halophenols and haloanilines
Bumagin, NA
Luzikova, EV
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 532 (1-2) : 271 - 273
[2] Cross-coupling of vinylpolysiloxanes with aryl iodides
Denmark, SE
Wang, ZG
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) : 372 - 375
[3] Vinylation of aryl bromides using an inexpensive vinylpolysiloxane
Denmark, SE
Butler, CR
[J]. ORGANIC LETTERS, 2006, 8 (01) : 63 - 66
[4] Highly hindered stilbenes
Fuson, RC
Denton, JJ
Best, CE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1943, 8 (01) : 64 - 72
[5] Cytosporone E: racemic synthesis and preliminary antibacterial testing
Hall, JD
Duncan-Gould, NW
Siddiqi, NA
Kelly, JN
Hoeferlin, LA
Morrison, SJ
Wyatt, JK
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (04) : 1409 - 1413
[6] HECK VERSUS SUZUKI PALLADIUM-CATALYZED CROSS-COUPLING OF A VINYLBORONATE ESTER WITH ARYL HALIDES
HUNT, AR
STEWART, SK
WHITING, A
[J]. TETRAHEDRON LETTERS, 1993, 34 (22) : 3599 - 3602
[7] Dendrimers based on a three-dimensionally disposed AB4 monomer
Jayakumar, KN
Bharathi, P
Thayumanavan, S
[J]. ORGANIC LETTERS, 2004, 6 (15) : 2547 - 2550
[8] Tetraalkylammonium salt-based catalyst systems for directing the arylation of vinyltrimethylsilane
Jeffery, T
[J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1673 - 1676
[9] A mild, efficient and selective deprotection of t-butyldimethylsilyl-protected phenols using cesium carbonate
Jiang, ZY
Wang, YG
[J]. TETRAHEDRON LETTERS, 2003, 44 (19) : 3859 - 3861
[10] Generation of substituted styrenes via Suzuki cross-coupling of aryl halides with 2,4,6-trivinylcyclotriboroxane
Kerins, F
O'Shea, DF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) : 4968 - 4971

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