Anion-functionalized ionic liquids enhance the CuI-Catalyzed cross-coupling reaction of sulfinic acid salts with aryl halides and vinyl bromides

被引:105
作者
Bian, Ming [1 ]
Xu, Fada [1 ]
Ma, Cheng [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
来源
SYNTHESIS-STUTTGART | 2007年 / 19期
关键词
ionic liquids; homogeneous catalysis; cross-coupling; copper; sulfones;
D O I
10.1055/s-2007-990778
中图分类号
O62 [有机化学];
学科分类号
070303 [有机化学]; 081704 [应用化学];
摘要
An easily accessible, anion-functionalized ionic liquid, 1-ethyl-3-methylimidazolium (S)-2-amino-3-methylbutyric acid salt, [emim] [Val], has been demonstrated to be an efficient additive for the CuI-catalyzed coupling reaction of sulfinic acid salts with aryl iodides, aryl bromides and vinyl bromides, leading to the formation of sulfones in good yields.
引用
收藏
页码:2951 / 2956
页数:6
相关论文
共 52 条
[1]
The copper-catalyzed N-arylation of indoles [J].
Antilla, JC ;
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688
[2]
Structure-based design, synthesis, and biological evaluation of navel pyrrolyl aryl sulfones: HIV-1 non-nucleoside reverse transcriptase inhibitors active at nanomolar concentrations [J].
Artico, M ;
Silvestri, R ;
Pagnozzi, E ;
Bruno, B ;
Novellino, E ;
Greco, G ;
Massa, S ;
Ettorre, A ;
Loi, AG ;
Scintu, F ;
La Colla, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (09) :1886-1891
[3]
An ionic liquid-supported ruthenium carbene complex: A robust and recyclable catalyst for ring-closing olefin metathesis in ionic liquids [J].
Audic, N ;
Clavier, H ;
Mauduit, M ;
Guillemin, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) :9248-9249
[4]
PREPARATION OF ALPHA-BETA-UNSATURATED SULFONES [J].
BALIAH, V ;
SESHAPATHIRAO, M .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (06) :867-868
[5]
Zinc-mediated fast sulfonylation of aromatics [J].
Bandgar, BP ;
Kasture, SP .
SYNTHETIC COMMUNICATIONS, 2001, 31 (07) :1065-1068
[6]
An efficient copper catalyst for the formation of sulfones from sulfinic acid salts and aryl iodides [J].
Baskin, JM ;
Wang, ZY .
ORGANIC LETTERS, 2002, 4 (25) :4423-4425
[7]
Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[8]
Ionic phosphine ligands with cobaltocenium backbone: Novel ligands for the highly selective, biphasic, rhodium-catalyzed hydroformylation of 1-octene in ionic liquids [J].
Brasse, CC ;
Englert, U ;
Salzer, A ;
Waffenschmidt, H ;
Wasserscheid, P .
ORGANOMETALLICS, 2000, 19 (19) :3818-3823
[9]
Unsymmetrical diaryl sulfones and aryl vinyl sulfones through palladium-catalyzed coupling of aryl and vinyl halides or triflates with sulfinic acid salts [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Parisi, LM ;
Bernini, R .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (17) :5608-5614
[10]
Unsymmetrical diaryl sulfones through palladium-catalyzed coupling of aryl iodides and arenesulfinates [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Parisi, LM .
ORGANIC LETTERS, 2002, 4 (26) :4719-4721