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Ruthenium(II)‐Catalyzed C−H Difluoromethylation of Ketoximes: Tuning the Regioselectivity from the meta to the para Position
Author(s) -
Yuan Chunchen,
Zhu Lei,
Zeng Runsheng,
Lan Yu,
Zhao Yingsheng
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711221
Subject(s) - ruthenium , chemistry , regioselectivity , catalysis , selectivity , yield (engineering) , chelation , combinatorial chemistry , organic chemistry , materials science , metallurgy
A highly para ‐selective C Ar −H difluoromethylation of ketoxime ethers under ruthenium catalysis has been developed. A wide variety of ketoxime ethers are compatible with the reaction, which leads to the corresponding para ‐difluoromethylated products in moderate to good yield. A mechanistic study clearly showed that chelation‐assisted cycloruthenation is the key factor in the para selectivity of the difluoromethylation of ketoxime ethers. Density functional theory was used to gain a theoretical understanding of the para selectivity.#