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Synthesis of ortho ‐(Fluoro)alkylated Pyridines via Visible Light‐Promoted Radical Isocyanide Insertion
Author(s) -
Tong Kun,
Zheng Tianyi,
Zhang Yan,
Yu Shouyun
Publication year - 2015
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.201500674
Subject(s) - chemistry , alkylation , isocyanide , reagent , pyridine , photochemistry , visible spectrum , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , physics , optoelectronics
A regiospecific synthesis of ortho ‐trifluoromethylated and ortho ‐(fluoro)alkylated pyridine derivatives has been developed. This strategy is enabled by visible light‐promoted vinyl isocyanide insertions with Umemoto’s reagent and electron‐deficient bromides at room temperature. The methodology presented here provides an access to highly functionalized ortho ‐(fluoro)alkylated pyridine derivatives regiospecifically under mild conditions with good yields. The proposed mechanism was supported by TEMPO trapping experiments, Stern–Volmer analysis and light off/on and time profile experiments.