Highly N2-Selective Palladium-Catalyzed Arylation of 1,2,3-Triazoles

被引：136

作者：

Ueda, Satoshi ^{[1
]}

Su, Mingjuan ^{[1
]}

Buchwald, Stephen L. ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 38期

基金：

美国国家卫生研究院;

关键词：

C-N coupling; heterocycles; homogeneous catalysis; N-arylation; palladium; NONACTIVATED TERMINAL ALKYNES; 3-COMPONENT COUPLING REACTION; EFFICIENT SYNTHESIS; CLICK CHEMISTRY; AZIDES; CYCLOADDITION; DISCOVERY;

D O I：

10.1002/anie.201103882

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A familiar ring? Highly N2-selective arylation of 4,5-unsubstituted and 4-substituted 1,2,3-triazoles was achieved for the first time by the Pd/1 catalyst system. A wide range of N2-aryl-1,2,3- triazoles were prepared from aryl bromides, chlorides, and triflates with excellent N2 selectivity (see scheme). Density functional theory calculations suggest that the formation of N2-arylated 1,2,3-triazoles is favored kinetically. dba=dibenzylideneacetone, Tf=trifluoromethanesulfonyl. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：8944 / 8947

页数：4

共 50 条

[1] Efficient N2-selective copper-catalyzed arylation of 1,2,3-triazoles
Ha, Khanh
Nasajpour, Amir C.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
[2] Palladium-Catalyzed C-H Arylation of 1,2,3-Triazoles
Zhang, Chengwei
You, Lin
Chen, Chuo
MOLECULES, 2016, 21 (10)
[3] Highly N2-Selective Coupling of 1,2,3-Triazoles with Indole and Pyrrole
Wen, Jian
Zhu, Li-Li
Bi, Qing-Wei
Shen, Zhu-Qing
Li, Xiao-Xiao
Li, Xin
Wang, Zhen
Chen, Zili
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (04) : 974 - 978
[4] BrØnsted acid catalyzed N2-selective alkylation of 1,2,3-triazoles with trichloroacetimidates
Lin, Wenhong
Chrissley, Jared M.
Chisholm, John D.
TETRAHEDRON LETTERS, 2024, 148
[5] Palladium-Catalyzed Regioselective C-5 Arylation of 1,2,3-Triazoles with Diaryliodonium Salts
Gang, Fangli
Che, Yang
Du, Zhengyin
Feng, Hua
Fu, Ying
SYNLETT, 2017, 28 (13) : 1624 - 1629
[6] Palladium-Catalyzed Dehydrogenative Direct Arylations of 1,2,3-Triazoles
Ackermann, Lutz
Jeyachandran, Rajkumar
Potukuchi, Harish K.
Novak, Petr
Buettner, Lea
ORGANIC LETTERS, 2010, 12 (09) : 2056 - 2059
[7] N2-Selective lodofunctionalization of Olefins with NH-1,2,3-Triazoles to provide N2-Alkyl-Substituted 1,2,3-Triazoles
Zhu, Li-Li
Xu, Xiao-Qi
Shi, Jin-Wei
Chen, Bai-Ling
Chen, Zili
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09): : 3568 - 3575
[8] Highly N2-selective allylation of NH-1,2,3-triazoles with allenamides mediated by N-iodosuccinimide
Man, Xi Jia Ai Ti Re He
Liu, Yong Chun
Li, Xiao Xiao
Zhao, Zhi Gang
NEW JOURNAL OF CHEMISTRY, 2019, 43 (37) : 14739 - 14746
[9] Palladium-Catalyzed Acylation of 2-Aryl-1,2,3-triazoles with Aldehydes
Wang, Zechao
Tian, Qinshan
Yu, Xin
Kuang, Chunxiang
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (05) : 961 - 966
[10] Transition metal free selective N2-arylation of 1,2,3-triazoles
Roshandel, Sahar
Lunn, Maiko
Suri, Suresh
Prakash, Surya
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258

← 1 2 3 4 5 →