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Rhodium‐Catalyzed Regioselective N 2 ‐Alkylation of Benzotriazoles with Diazo Compounds/Enynones via a Nonclassical Pathway
Author(s) -
Wang Kai,
Chen Ping,
Ji Danqing,
Zhang Xinhao,
Xu Guangyang,
Sun Jiangtao
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807039
Subject(s) - alkylation , rhodium , diazo , regioselectivity , chemistry , carbene , catalysis , medicinal chemistry , organic chemistry
A novel rhodium‐catalyzed highly selective N 2 ‐alkylation of benzotriazoles with diazo compounds/enynones is achieved, providing N 2 ‐alkylated benzotriazoles in good to excellent yields and with excellent N 2 selectivities. Importantly, different to traditional carbene insertion into X−H (X=N, O etc) bonds, DFT calculations disclose that this selective N 2 ‐alkylation probably proceeds through a formal 1,3‐ rather than 1,2‐H shift to give the final products.