A mild and efficient new synthesis of aryl sulfones from boronic acids and sulfinic acid salts

被引:65
作者
Beaulieu, C
Guay, D
Wang, ZY
Evans, DA
机构
[1] Merck Frosst Ctr Therapeut Res, Dept Med Chem, Pointe Claire, PQ H9R 4P8, Canada
[2] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
关键词
aryl sulfone; cross-coupling reaction; boronic acid;
D O I
10.1016/j.tetlet.2004.02.127
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new efficient and mild preparation of sulfones from boronic acids and sulfinic acid salts is reported. The cross-coupling reaction mediated by cupric acetate gives access to a variety of sulfones in excellent yield. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3233 / 3236
页数:4
相关论文
共 14 条
[1]   REACTIONS OF ORGANOLITHIUM COMPOUNDS WITH SULFONATE ESTERS - NOVEL SULFONE SYNTHESIS [J].
BAARSCHERS, WH .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (19) :3056-3059
[2]   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
[3]   An efficient palladium-catalyzed synthesis of unsymmetrical diaryl sulfones from aryl bromides/triflates and arenesulfinates [J].
Cacchi, S ;
Fabrizi, G ;
Goggiamani, A ;
Parisi, LM .
SYNLETT, 2003, (03) :361-364
[4]   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
[5]   Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine [J].
Evans, DA ;
Katz, JL ;
West, TR .
TETRAHEDRON LETTERS, 1998, 39 (19) :2937-2940
[6]  
Gilman H., 1925, J AM CHEM SOC, V47, P2047, DOI [10.1021/ja01684a040, DOI 10.1021/JA01684A040]
[7]   SYNTHESIS OF ARYL SULFONES [J].
GRAYBILL, BM .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (09) :2931-&
[8]   Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols [J].
Herradura, PS ;
Pendola, KA ;
Guy, RK .
ORGANIC LETTERS, 2000, 2 (14) :2019-2022
[9]   New aryl/heteroaryl C-N bond cross-coupling reactions via arylboronic acid cupric acetate arylation [J].
Lam, PYS ;
Clark, CG ;
Saubern, S ;
Adams, J ;
Winters, MP ;
Chan, DMT ;
Combs, A .
TETRAHEDRON LETTERS, 1998, 39 (19) :2941-2944
[10]   The discovery of rofecoxib, [MK 966, Vioxx®, 4-(4′-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2 inhibitor [J].
Prasit, P ;
Wang, Z ;
Brideau, C ;
Chan, CC ;
Charleson, S ;
Cromlish, W ;
Ethier, D ;
Evans, JF ;
Ford-Hutchinson, AW ;
Gauthier, JY ;
Gordon, R ;
Guay, J ;
Gresser, M ;
Kargman, S ;
Kennedy, B ;
Leblanc, Y ;
Léger, S ;
Mancini, J ;
O'Neill, GP ;
Ouellet, M ;
Percival, MD ;
Perrier, H ;
Riendeau, D ;
Rodger, I ;
Tagari, P ;
Thérien, M ;
Vickers, P ;
Wong, E ;
Xu, LJ ;
Young, RN ;
Zamboni, R ;
Boyce, S ;
Rupniak, N ;
Forrest, N ;
Visco, D ;
Patrick, D .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (13) :1773-1778