Copper-catalyzed synthesis of N-sulfonyl-1,2,3-triazoles:: Controlling selectivity

被引:303
作者
Yoo, Eun Jeong
Ahlquist, Marten
Kim, Seok Hwan
Bae, Imhyuck
Fokin, Valery V. [1 ]
Sharpless, K. Barry
Chang, Sukbok
机构
[1] Korea Adv Inst Sci & Technol, Dept Chem, CMDS, Taejon 305701, South Korea
[2] Korea Adv Inst Sci & Technol, Sch Mol Sci BK21, Taejon 305701, South Korea
[3] Kemitorvet Technical Univ Denmark, Dept Chem, DK-2888 Lyngby, Denmark
[4] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[5] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
关键词
alkynes; copper; cycloaddition; sulfonyl azides; sulfonyltriazoles;
D O I
10.1002/anie.200604241
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) 4-Substituted 1-(N-sulfonyl)-1,2,3-triazoles are selectively obtained by using the Cu-catalyzed azide-alkyne cycloaddition reaction with sulfonyl azides. Performing the reaction at 0°C in chloroform in the presence of 2,6-lutidine and Cul as the catalyst effectively prevents the ketenimine pathway and provides convenient access to N-sulfonyltriazoles in good to excellent yields. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1730 / 1733
页数:4
相关论文
共 38 条
[1]  
Ashry E.S.H.E., 1999, ADV HETEROCYCL CHEM, V75, P79
[2]   Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine [J].
Bae, I ;
Han, H ;
Chang, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2038-2039
[3]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[4]  
Cassidy M.P., 2006, ANGEW CHEM, V118, P3226
[5]   Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides [J].
Cassidy, Michael P. ;
Raushel, Jessica ;
Fokin, Valery V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3154-3157
[6]   Catalytic one-pot synthesis of cyclic amidines by virtue of tandem reactions involving intramolecular hydroamination under mild conditions [J].
Chang, Sukbok ;
Lee, Minjae ;
Jung, Doo Young ;
Yoo, Eun Jeong ;
Cho, Seung Hwan ;
Han, Sun Kyu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (38) :12366-12367
[7]   Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water [J].
Cho, SH ;
Yoo, EJ ;
Bae, L ;
Chang, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16046-16047
[8]  
Dimroth O, 1909, LIEBIGS ANN CHEM, V364, P183
[9]   HETEROCYCLISCHE SYNTHESEN MIT ATHOXYACETYLEN .3. UBER ALPHA-DIAZO-N-SULFONYL-ACETIMIDSAUREESTER [J].
GRUNANGER, P ;
FINZI, PV ;
SCOTTI, C .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (02) :623-+
[10]  
Grunanger P., 1963, TETRAHEDRON LETT, V4, P1839