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Rhodium‐Catalyzed Synthesis of 4‐Bromo‐1,2‐dihydroisoquinolines: Access to Bromonium Ylides by the Intramolecular Reaction of a Benzyl Bromide and an α‐Imino Carbene
Author(s) -
He Jun,
Shi Yinping,
Cheng Wanli,
Man Zengming,
Yang Dongdong,
Li ChuanYing
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201512015
Subject(s) - rhodium , carbene , intramolecular force , ylide , chemistry , bromide , nucleophile , catalysis , medicinal chemistry , intramolecular reaction , sulfonyl , organic chemistry , alkyl
Abstract Highly functionalized 4‐bromo‐1,2‐dihydroisoquinolines were synthesized from readily available 4‐(2‐(bromomethyl)phenyl)‐1‐sulfonyl‐1,2,3‐triazoles. A bromonium ylide is proposed as the key intermediate, which can be formed by the intramolecular nucleophilic attack of the benzyl bromide on the α‐imino rhodium carbene formed in the presence of the rhodium catalyst.