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Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water
Author(s) -
Yang Liu,
Huang Zhiyan,
Li Gang,
Zhang Wei,
Cao Rui,
Wang Chao,
Xiao Jianliang,
Xue Dong
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201710698
Subject(s) - aryl , chemistry , hydroxylation , catalysis , phenols , deprotonation , halide , nickel , ligand (biochemistry) , intramolecular force , organic chemistry , combinatorial chemistry , ion , biochemistry , alkyl , receptor , enzyme
A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble‐metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.