B-alkylcatecholboranes as a source of radicals for efficient conjugate additions and allylations

被引:21
作者
Schaffner, AP [1 ]
Becattini, B [1 ]
Ollivier, C [1 ]
Weber, V [1 ]
Renaud, P [1 ]
机构
[1] Univ Bern, Dept Chem & Biochem, CH-3000 Bern 9, Switzerland
来源
SYNTHESIS-STUTTGART | 2003年 / 17期
关键词
radicals; tin-free; hydroboration; allylation; conjugate addition;
D O I
10.1055/s-2003-42430
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
B-Alkylcatecholboranes, easily prepared in situ by hydroboration of alkenes, are powerful radical precursors that can be used for carbon-carbon bond formation. Typical procedures for (a) conjugate addition to enones, (b) conjugate addition to activated alkenes such as vinyl sulfones, and (c) direct allylation are described. Experimentally, these three one-pot reactions are easy to perform. No slow addition of a reagent, a procedure frequently encountered in intermolecular radical additions, is required.
引用
收藏
页码:2740 / 2742
页数:3
相关论文
共 13 条
[1]  
Becattini B, 2003, SYNLETT, P1485
[2]   Free-radical hydroxylation reactions of alkylboronates [J].
Cadot, C ;
Dalko, PI ;
Cossy, J ;
Ollivier, C ;
Chuard, R ;
Renaud, P .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7193-7202
[3]   Radical carbon-carbon coupling reactions via organoboranes [J].
Cadot, C ;
Cossy, J ;
Dalko, PI .
CHEMICAL COMMUNICATIONS, 2000, (12) :1017-1018
[4]  
GARETT CE, 1996, J ORG CHEM, V61, P3224
[5]  
Ollivier C, 1999, CHEM-EUR J, V5, P1468, DOI 10.1002/(SICI)1521-3765(19990503)5:5<1468::AID-CHEM1468>3.0.CO
[6]  
2-7
[7]  
Ollivier C, 1999, SYNLETT, P807
[8]   Organoboranes as a source of radicals [J].
Ollivier, C ;
Renaud, P .
CHEMICAL REVIEWS, 2001, 101 (11) :3415-3434
[9]  
Ollivier C, 2000, ANGEW CHEM INT EDIT, V39, P925, DOI 10.1002/(SICI)1521-3773(20000303)39:5<925::AID-ANIE925>3.0.CO
[10]  
2-M