Rapid and mild sulfonylation of aromatic compounds with sulfonic acids via mixed anhydrides using Tf2O

被引:34
作者
Alizadeh, Abdolhamid [1 ]
Khodaei, Mohammd Mehdi [1 ]
Nazari, Ehsan [1 ]
机构
[1] Razi Univ, Fac Sci, Dept Chem, Kermanshah 67149, Iran
关键词
sulfonylation; sulfones; sulfonic acids; Tf2O; aromatic compounds;
D O I
10.1016/j.tetlet.2007.07.081
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient and direct sulfonylation of aromatic compounds with sulfonic acids is described via mixed anhydrides in short reaction times using Tf2O in nitromethane at room temperature. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6805 / 6808
页数:4
相关论文
共 24 条
[1]   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
[2]   Sodium periodate catalyzed selective sulfonylation of aromatics [J].
Bandgar, BP ;
Kamble, VT .
CHEMISTRY LETTERS, 2002, (10) :1066-1067
[3]   Friedel-Crafts sulfonylation of aromatics catalysed by solid acids: An eco-friendly route for sulfone synthesis [J].
Choudary, BM ;
Chowdari, NS ;
Kantam, ML .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16) :2689-2693
[4]   SULFONYLATION OF ORGANOMETALLIC REAGENTS WITH ARENESULFONYL FLUORIDES - A SIMPLE ONE-STEP SYNTHESIS OF SULFONES [J].
FRYE, LL ;
SULLIVAN, EL ;
CUSACK, KP ;
FUNARO, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :697-701
[5]   SYNTHESIS OF ARYL SULFONES [J].
GRAYBILL, BM .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (09) :2931-&
[6]  
HASTINGS RC, 1966, ANN REV PHARM TOXICO, V28, P231
[7]  
Jin TS, 2003, J CHEM RES, P721
[8]   Tf2O as a rapid and efficient promoter for the dehydrative Friedel-Crafts acylation of aromatic compounds with carboxylic acids [J].
Khodaei, Mohammd Mehdi ;
Alizadeh, Abdolhamid ;
Nazari, Ehsan .
TETRAHEDRON LETTERS, 2007, 48 (24) :4199-4202
[9]  
Li HZ, 2003, J CHEM RES, P493
[10]   TREATMENT OF DISCOID LUPUS-ERYTHEMATOSUS [J].
LO, JS ;
BERG, RE ;
TOMECKI, KJ .
INTERNATIONAL JOURNAL OF DERMATOLOGY, 1989, 28 (08) :497-507