Palladium-catalyzed cross-coupling alkylation of arenediazonium o-benzenedisulfonimides

被引:14
作者
Barbero, Margherita [1 ]
Cadamuro, Silvano [1 ]
Dughera, Stefano [1 ]
机构
[1] Univ Turin, Dipartimento Chim Gen & Organ Applicata, I-10125 Turin, Italy
来源
SYNTHESIS-STUTTGART | 2008年 / 3卷 / 03期
关键词
palladium; Stille reaction; suzuki reaction; crosscoupling; diazo compounds;
D O I
10.1055/s-2008-1032027
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Arenediazonium o-benzenedisulfonimides were reacted with tetramethyltin, tetrabutyltin or trialkylboranes. The reactions, carried out in the presence of palladium(II) derivatives as precatalysts, gave the methylation and alkylation products with good overall conversions. The o-benzenedisulfonimide was recovered in high yield from all the reactions and could be recycled for the preparation of other salts.
引用
收藏
页码:474 / 478
页数:5
相关论文
共 33 条
[1]   Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling [J].
Andrus, MB ;
Song, C .
ORGANIC LETTERS, 2001, 3 (23) :3761-3764
[2]   Arenediazonium o-benzenedisulfonimides as efficient reagents for Heck-type arylation reactions [J].
Artuso, E ;
Barbero, M ;
Degani, I ;
Dughera, S ;
Fochi, R .
TETRAHEDRON, 2006, 62 (13) :3146-3157
[3]   Hydrodediazoniation of dry arenediazonium o-benzenedisulfonimides with hydrogen peroxide [J].
Barbero, M ;
Degani, I ;
Dughera, S ;
Fochi, R .
SYNTHESIS-STUTTGART, 2004, (14) :2386-2390
[4]  
Barbero M, 1998, SYNTHESIS-STUTTGART, P1171
[5]   Arenediazonium o-benzenedisulfonimides in Heck-type arylation of allylic alcohols [J].
Barbero, Margherita ;
Cadamuro, Silvano ;
Dughera, Stefano .
SYNTHESIS-STUTTGART, 2006, (20) :3443-3452
[6]   Reactions of dry arenediazionium o-benzenedisulfonimides with triorganoindium compounds [J].
Barbero, Margherita ;
Cadamuro, Silvano ;
Dughera, Stefano ;
Giaveno, Cinzia .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (21) :4884-4890
[7]   THE PREPARATION OF THE C-10 MONOCYCLIC AROMATIC HYDROCARBONS [J].
BIRCH, SF ;
DEAN, RA ;
FIDLER, FA ;
LOWRY, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (04) :1362-1369
[8]   DISTRIBUTION OF ISOMERS IN THE MONONITRATION OF ETHYLBENZENE AND ISOPROPYLBENZENE - FURTHER EVIDENCE FOR A STERIC EFFECT IN ISOMER DISTRIBUTION [J].
BROWN, HC ;
BONNER, WH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (02) :605-606
[9]   INFRARED INTENSITIES AS A QUANTITATIVE MEASURE OF INTRAMOLECULAR INTERACTIONS .26. VARIABLE RESONANCE BEHAVIOR BY ALKYL AND SUBSTITUTED ALKYL-GROUPS [J].
BROXTON, TJ ;
CAMERON, DG ;
TOPSOM, RD ;
KATRITZK.AR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (03) :256-260
[10]  
BUMAGIN NA, 1994, RUSS J ORG CHEM+, V30, P1605