Cross-coupling reactions of potassium alkyltrifluoroborates with aryl and 1-alkenyl trifluoromethanesulfonates

被引:204
作者
Molander, GA [1 ]
Ito, T [1 ]
机构
[1] Univ Penn, Roy & Diana Vagelos Labs, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/ol006896u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The palladium-catalyzed coupling reaction of potassium alkyltrifluoroborates with aryl- or alkenyltriflates proceeds to afford the corresponding arenes or alkenes in high yield. The berates are all solids, stable in air, and thus can be stored on the shelf indefinitely. The cross coupling can be effected using PdCl2(dppf). CH2Cl2 as the catalyst in THF-H2O in the presence of CS2CO3 A variety of functional groups can be tolerated within the berate and/or the triflate coupling partner.
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页码:393 / 396
页数:4
相关论文
共 48 条
[1]   Alkenyl and aryl boronates -: Mild nucleophiles for the stereoselective formation of functionalized N-heterocycles [J].
Batey, RA ;
MacKay, DB ;
Santhakumar, V .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :5075-5076
[2]   Potassium allyl- and crotyltrifluoroborates: Stable and efficient agents for allylation and crotylation [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
TETRAHEDRON LETTERS, 1999, 40 (23) :4289-4292
[3]   Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
ORGANIC LETTERS, 1999, 1 (10) :1683-1686
[4]  
Batey RA, 2000, SYNTHESIS-STUTTGART, P990
[5]   ORGANOBORANES .30. CONVENIENT PROCEDURES FOR THE SYNTHESIS OF ALKYLBORONIC AND ALKENYLBORONIC ACIDS AND ESTERS [J].
BROWN, HC ;
BHAT, NG ;
SOMAYAJI, V .
ORGANOMETALLICS, 1983, 2 (10) :1311-1316
[6]   TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS [J].
BURGESS, K ;
OHLMEYER, MJ .
CHEMICAL REVIEWS, 1991, 91 (06) :1179-1191
[7]   A novel stereocontrolled synthesis of 1,2-trans cyclopropyl ketones via Suzuki-type coupling of acid chlorides with cyclopropylboronic acids [J].
Chen, H ;
Deng, MZ .
ORGANIC LETTERS, 2000, 2 (12) :1649-1651
[8]   Cross-coupling reactions of arenediazonium tetrafluoroborates with potassium aryl- or alkenyltrifluoroborates catalyzed by palladium [J].
Darses, S ;
Genet, JP ;
Brayer, JL ;
Demoute, JP .
TETRAHEDRON LETTERS, 1997, 38 (25) :4393-4396
[9]   Potassium vinyltrifluoroborate:: A stable and efficient vinylating agent of arenediazonium salts using palladium catalysts [J].
Darses, S ;
Michaud, G ;
Genêt, JP .
TETRAHEDRON LETTERS, 1998, 39 (28) :5045-5048
[10]  
Darses S, 1999, EUR J ORG CHEM, V1999, P1875