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Gold‐Catalyzed One‐Pot Synthesis of Polyfluoroalkylated Oxazoles from N‐Propargylamides Under Visible‐Light Irradiation
Author(s) -
Liu Yantao,
Shi Yating,
Wei Lanen,
Zhao Ke,
Zhao Jingjing,
Zhang Puyu,
Xu Xuejun,
Li Pan
Publication year - 2021
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.202100614
Subject(s) - catalysis , homolysis , radical , irradiation , visible spectrum , photochemistry , chemistry , compatibility (geochemistry) , combinatorial chemistry , materials science , organic chemistry , optoelectronics , physics , nuclear physics , composite material
A gold‐catalyzed synthesis of polyfluoroalkylated oxazoles from N‐propargylamides under visible‐light irradiation has been developed. These reactions display excellent compatibility of radicals and gold catalysts under visible‐light irradiation. Mechanistic experiments indicate that polyfluoroalkyl iodides play a dual role in enhanced compatibility of radicals and gold catalysts through assisted protodeauration of vinyl gold and reactivated the gold catalyst. In addition, PPh 3 AuNTf 2 not only activates N‐propargylamide to generate vinyl gold intermediate, but also greatly promotes homolysis of polyfluoroalkyl iodides under blue light irradiation.