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Copper‐Catalyzed Cyclization of Aryl Amines and Aryldiazonium Salts under Air: Access to N ‐2‐Aryl‐Naphthotriazoles
Author(s) -
Zhu Chuanle,
Zeng Hao,
Chen Fulin,
Liu Chi,
Jiang Huanfeng
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900981
Subject(s) - chemistry , aryl , catalysis , moiety , copper , combinatorial chemistry , bond cleavage , organic chemistry , medicinal chemistry , alkyl
A catalytic and step economic protocol for the construction of N ‐2‐aryl‐naphthotriazoles via copper‐catalyzed cyclization of aryl amines and aryldiazonium salts is reported. With dioxygen in the air as termial oxidants under copper catalysis, various N ‐2‐aryl‐naphthotriazoles were synthesized in high yields. Importantly, this protocol features the sufficient inhibition of the classic C‐N 2 bond cleavage process of aryldiazonium tetrafluoroborates under copper catalysis and the undesired dehydrogenative coupling of aryl amines under oxidative conditions. Preliminary mechanistic studies indicated that a radical procedure might not be involved in this transformation. In addition, simple decoration of the obtained compounds delivers novel and attractive tetraphenylethylene moiety containing N ‐2‐aryl‐naphthotriazole derivatives.