Potassium alkenyl- and aryltrifluoroborates: Stable and efficient agents for rhodium-catalyzed addition to aldehydes and enones

被引:184
作者
Batey, RA [1 ]
Thadani, AN [1 ]
Smil, DV [1 ]
机构
[1] Univ Toronto, Dept Chem, Lash Miller Chem Labs, Toronto, ON M5S 3H6, Canada
关键词
D O I
10.1021/ol9910767
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Potassium alkenyl- and aryltrifluoroborates undergo addition to enones and aldehydes in the presence of Rh(1) catalysts to give beta-functionalized ketones and allylic/benzylic alcohols, respectively. Reaction proceeds more rapidly than with the corresponding boronic acids, and the choice of phosphine ligand does not signifcantly influence the overall efficiency of addition.
引用
收藏
页码:1683 / 1686
页数:4
相关论文
共 20 条
[1]   Diels-Alder reactions of dienylboron compounds with unactivated dienophiles: an application of boron tethering for substituted cyclohexenol synthesis [J].
Batey, RA ;
Thadani, AN ;
Lough, AJ .
CHEMICAL COMMUNICATIONS, 1999, (05) :475-476
[2]   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
[3]   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
[4]  
Batey RA, 1999, ANGEW CHEM INT EDIT, V38, P1798, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1798::AID-ANIE1798>3.0.CO
[5]  
2-0
[6]   Alkenylboronate tethered intramolecular Diels-Alder reactions [J].
Batey, RA ;
Thadani, AN ;
Lough, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (02) :450-451
[7]   SOME SALTS OF TRIFLUOROMETHYLFLUOROBORIC ACID [J].
CHAMBERS, RD ;
CLARK, HC ;
WILLIS, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (20) :5298-5301
[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