Copper-in-Charcoal-Catalyzed, Tandem One-Pot Diazo Transfer-Click Reactions

被引:61
作者
Lee, Ching-Tien [1 ]
Huang, Shenlin [1 ]
Lipshutz, Bruce H. [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
关键词
click chemistry; copper-in-charcoal; diazo transfer; heterogeneous catalysis; AZIDES; 1,2,3-TRIAZOLES; CYCLOADDITION;
D O I
10.1002/adsc.200900604
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Copper-in-charcoal (Cu/C) is an effective heterogeneous catalyst for tandem diazo transfer/click reactions. In the presence of Cu/C, various azides can be generated in situ from the corresponding amines, and subsequently undergo [3+2]cycloaddition with terminal alkynes to afford tri-azoles in good yields. The catalyst is also easily recycled.
引用
收藏
页码:3139 / 3142
页数:4
相关论文
共 23 条
[1]   Metal catalyzed diazo transfer for the synthesis of azides from amines [J].
Alper, PB ;
Hung, SC ;
Wong, CH .
TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032
[2]   Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages [J].
Barral, Karine ;
Moorhouse, Adam D. ;
Moses, John E. .
ORGANIC LETTERS, 2007, 9 (09) :1809-1811
[3]   One-pot procedure for diazo transfer and azide-alkyne cycloaddition: Triazole linkages from amines [J].
Beckmann, Henning S. G. ;
Wittmann, Valentin .
ORGANIC LETTERS, 2007, 9 (01) :1-4
[4]   Organic azides:: An exploding diversity of a unique class of compounds [J].
Bräse, S ;
Gil, C ;
Knepper, K ;
Zimmermann, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) :5188-5240
[5]  
Brase S., 2005, ANGEW CHEM, V117, P5320, DOI DOI 10.1002/ANGE.200400657
[6]   One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from in situ generated azides [J].
Feldman, AK ;
Colasson, B ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (22) :3897-3899
[7]   Dendronized linear polymers via "click chemistry" [J].
Helms, B ;
Mynar, JL ;
Hawker, CJ ;
Fréchet, JMJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15020-15021
[8]  
Huisgen R., 1963, Angew. Chem. Int. Ed, V2, P565, DOI [DOI 10.1002/ANIE.196305651, 10.1002/anie.196305651]
[9]   Efficient one-pot synthesis of 1,2,3-triazoles from benzyl and alkyl halides [J].
Kacprzak, K .
SYNLETT, 2005, (06) :943-946
[10]   A potent and highly selective inhibitor of human α-1,3-fucosyltransferase via click chemistry [J].
Lee, LV ;
Mitchell, ML ;
Huang, SJ ;
Fokin, VV ;
Sharpless, KB ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) :9588-9589