Reliable and Diverse Synthesis of Aryl Azides through Copper-Catalyzed Coupling of Boronic Acids or Esters with TMSN3

被引：80

作者：

Li, Yu ^{[1
,2
]}

Gao, Lian-Xun ^{[1
]}

Han, Fu-She ^{[1
]}

机构：

[1] Chinese Acad Sci, Changchun Inst Appl Chem, Changchun 130022, Jilin, Peoples R China

[2] Chinese Acad Sci, Grad Sch, Beijing 100864, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2010年 / 16卷 / 27期

关键词：

aryl azides; boronic acids; boronic esters; copper; cross-coupling; HUISGEN 1,3-DIPOLAR CYCLOADDITION; CLICK CHEMISTRY APPROACH; TETRAZOLE FORMATION; AROMATIC-AMINES; REACTIVITY; AZIRIDINES; CONVERSION; COMPLEXES; NITRILES; CYANIDES;

D O I：

10.1002/chem.201000971

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) Aryl azide formation: The copper-catalyzed coupling reaction of boronic esters and acids with TMSN3 have been presented as a highly efficient, simple, broadly applicable, and less hazardous methodology for the practi cal synthesis of aryl azides with structural diversity (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：7969 / 7972

页数：4

共 47 条

[1] [Anonymous], ANGEW CHEM
[2] [Anonymous], 2002, Angew. Chem
[3] Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages
Barral, Karine
Moorhouse, Adam D.
Moses, John E.
[J]. ORGANIC LETTERS, 2007, 9 (09) : 1809 - 1811
[4] Bayley H., 1984, AZIDES NITRENES, P433
[5] Organic azides:: An exploding diversity of a unique class of compounds
Bräse, S
Gil, C
Knepper, K
Zimmermann, V
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5188 - 5240
[6] Brase S., 2005, ANGEW CHEM, V117, P5320, DOI DOI 10.1002/ANGE.200400657
[7] Azide-alkyne coupling:: A powerful reaction for bioconjugate chemistry
Breinbauer, R
Köhn, M
[J]. CHEMBIOCHEM, 2003, 4 (11) : 1147 - 1149
[8] Polymer-supported copper complex for C-N and C-O cross-coupling reactions with aryl boronic acids
Chiang, GCH
Olsson, T
[J]. ORGANIC LETTERS, 2004, 6 (18) : 3079 - 3082
[9] An easy access to aryl azides from aryl amines under neutral conditions
Das, J
Patil, SN
Awasthi, R
Narasimhulu, CP
Trehan, S
[J]. SYNTHESIS-STUTTGART, 2005, (11): : 1801 - 1806
[10] Demko ZP, 2002, ANGEW CHEM INT EDIT, V41, P2110, DOI 10.1002/1521-3773(20020617)41:12<2110::AID-ANIE2110>3.0.CO

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