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Palladium‐Catalyzed Intramolecular Self‐Alkylation of Polyfluoroarene via Heck and Decarboxylation Process
Author(s) -
Wei WanXu,
Chen Si,
Xia Yu,
Li Ming,
Li XueSong,
Han YaPing,
Wang CuiTian,
Liang YongMin
Publication year - 2019
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201900303
Subject(s) - decarboxylation , palladium , chemistry , catalysis , intramolecular force , heck reaction , combinatorial chemistry , alkylation , cascade reaction , organic chemistry
Abstract An efficient palladium‐catalyzed cyclization and polyfluorophenylation of γ,δ ‐unsaturated polyfluorobenzoyl oxime ester via iminopalladation/polyfluorobenzoyloxy decarboxylation cascade reaction is developed. The protocol provides a practical and atom‐economical access to a broad scope of various polyfluorophenylated dihydropyrrole derivatives. The reaction effectively utilizes the polyfluorobenzoyloxy leaving group as polyfluorophenylated source for the first time, precluding the need of additional polyfluoroarene. This is the first example of the introduction of electron‐deficient arenes in the further transformation of Narasaka‐Heck‐type reaction. Additionally, the reaction is conducted in a short time.