Premium
Gold‐Catalyzed Fluorination–Hydration: Synthesis of α‐Fluorobenzofuranones from 2‐Alkynylphenol Derivatives
Author(s) -
Wang Qiang,
Jiang Yu,
Sun Run,
Tang XiangYing,
Shi Min
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602545
Subject(s) - selectfluor , tetrafluoroborate , catalysis , octane , chemistry , redox , catalytic cycle , salt (chemistry) , combinatorial chemistry , organic chemistry , ionic liquid
The Au I ‐catalyzed fluorination–hydration of 2‐alkynylphenol derivatives in the presence of Selectfluor [1‐chloromethyl‐4‐fluoro‐1,4‐diazoniabicyclo‐[2.2.2]octane bis(tetrafluoroborate)] has been developed. This method provides straightforward access to α‐fluorobenzofuranones with the construction of C−O, C=O, and C−F bonds in a single step on the basis of an Au I /Au III redox catalytic cycle. Several control experiments, including the asymmetric variant of this reaction, were also conducted to gain insight into the reaction mechanism.