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Copper(I)‐Catalyzed Interrupted Click/Sulfenylation Cascade: One‐Pot Synthesis of Sulfur Cycle Fused 1,2,3‐Triazoles
Author(s) -
Wang Weiguo,
Huang Shuai,
Yan Shikun,
Sun Xuejun,
Tung ChenHo,
Xu Zhenghu
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900556
Subject(s) - chemistry , regioselectivity , cycloaddition , intramolecular force , catalysis , click chemistry , alkyne , cascade reaction , combinatorial chemistry , functional group , copper , substrate (aquarium) , azide , sulfur , catalytic cycle , tandem , organic chemistry , oceanography , materials science , composite material , geology , polymer
Summary of main observation and conclusion Herein, we report a practical protocol for the synthesis of sulfur cycle fused 1,2,3‐triazoles through a copper(I)‐catalyzed tandem click/intramolecular sulfenylation reaction. The reaction proceeded via a copper‐catalyzed alkyne azide cycloaddition, followed by interception of the in situ formed cuprate‐triazole intermediate with p ‐toluenesulfonothioate. This reaction shows broad substrate scope, complete regioselectivity, and excellent functional group tolerance under mild reaction conditions.