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Regiospecific Synthesis of 1‐Trifluoromethylisoquinolines Enabled by Photoredox Somophilic Vinyl Isocyanide Insertion
Author(s) -
Cheng Yuanzheng,
Yuan Xiangai,
Jiang Heng,
Wang Ruzhi,
Ma Jing,
Zhang Yan,
Yu Shouyun
Publication year - 2014
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.201400504
Subject(s) - isocyanide , chemistry , reagent , combinatorial chemistry , migratory insertion , photoredox catalysis , photochemistry , organic chemistry , photocatalysis , catalysis
A strategy has been developed for the regiospecific synthesis of 1‐trifluoromethylisoquinoline derivatives. This strategy is enabled by a photoredox vinyl isocyanide insertion with the help of Umemoto’s reagent. The methodology presented here provides an access to highly fuctionalized 1‐trifluoromethylisoquinolines regiospecifically under mild conditions in good‐to‐excellent chemical yields. A detailed mechanism is proposed, which is supported by experiments and theoretical calculations.