Direct synthesis of sulfonamides and activated sulfonate esters from sulfonic acids

被引：175

作者：

Caddick, S ^{[1
]}

Wilden, JD ^{[1
]}

Judd, DB ^{[1
]}

机构：

[1] UCL, Dept Chem, Christopher Ingold Labs, London WC1H 0AJ, England

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 04期

关键词：

D O I：

10.1021/ja0397658

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general new method for the preparation of sulfonamides and activated sulfonate esters by the direct coupling of sulfonic acid salts with amines and alcohols using the reagent triphenylphosphine ditriflate is described. A new reusable polymer-supported reagent for these transformations under heterogeneous conditions is also described. These methods provide a fundamentally new approach to making small molecules containing the sulfonamide functional group. Copyright © 2004 American Chemical Society.

引用

页码：1024 / 1025

页数：2

共 16 条

[1]

AABERG A, 1979, TETRAHEDRON LETT, P2263

[2] Solid-phase intermolecular radical reactions 2:: Synthesis of C-glycopeptide mimetics via a novel acrylate acceptor [J].

Caddick, S ;

Hamza, D ;

Wadman, SN ;

Wilden, JD .

ORGANIC LETTERS, 2002, 4 (10) :1775-1777

[3] A new route to sulfonamides via intermolecular radical addition to pentafluorophenyl vinylsulfonate and subsequent aminolysis [J].

Caddick, S ;

Wilden, JD ;

Bush, HD ;

Wadman, SN ;

Judd, DB .

ORGANIC LETTERS, 2002, 4 (15) :2549-2551

[4]

Frost CG, 2002, SYNLETT, P1928

[5]

Hansch C, 1990, COMPREHENSIVE MED CH, V1-6

[6] Cyclic sulfonamides via the ring-closing metathesis reaction [J].

Hanson, PR ;

Probst, DA ;

Robinson, RE ;

Yau, M .

TETRAHEDRON LETTERS, 1999, 40 (26) :4761-4764

[7]

HENDRICKSON JB, 1975, TETRAHEDRON LETT, P277

[8] The reversed Kenner linker:: A new safety-catch linker for the preparation of N-alkyl sulfonamides [J].

Maclean, D ;

Hale, R ;

Chen, MY .

ORGANIC LETTERS, 2001, 3 (19) :2977-2980

[9]

McKenzie R., 1996, INT J ALGEBR COMPUT, V6, P1

[10]

Mohamed SK, 2000, AFINIDAD, V57, P451

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