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Rhodium(III)‐Catalyzed Synthesis of Cinnolinium Salts from Azobenzenes and Diazo Compounds
Author(s) -
Chen Xiaohong,
Zheng Guangfan,
Song Guoyong,
Li Xingwei
Publication year - 2018
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.201800326
Subject(s) - trifluoromethanesulfonate , chemistry , diazo , rhodium , catalysis , zinc , alkylation , lewis acids and bases , coupling reaction , organic chemistry , combinatorial chemistry , polymer chemistry , medicinal chemistry
A Rh(III)‐catalyzed C−H activation of azobenzenes in the coupling with diazo compounds has been realized, providing a straightforward strategy to access functionalized cinnolinium triflates in high yields. This protocol features silver free mild reaction conditions and compatibility with diverse functional groups. The coupling proceeds via initial Rh(III)‐catalyzed C−H alkylation, followed by zinc triflate‐mediated cyclization, where zinc triflate acts as a Lewis acid as well as a triflate source.