Premium
Nickel‐Catalyzed One‐Pot Suzuki–Miyaura Cross‐Coupling of Phenols and Arylboronic Acids Mediated by N , N ‐Ditosylaniline
Author(s) -
Chen Liangshun,
Lang Hongyue,
Fang Lei,
Zhu Mengyun,
Liu Jinqian,
Yu Jianjun,
Wang Limin
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402475
Subject(s) - chemistry , phenols , aryl , reagent , catalysis , nickel , organic chemistry , combinatorial chemistry , medicinal chemistry , alkyl
An efficient method for the construction of two distinct C aryl –C aryl bonds through the Ni‐catalyzed Suzuki–Miyaura cross‐coupling of phenols with arylboronic acids has been developed. This reaction proceeds through the in situ tosylation of phenols by using N , N ‐ditosylaniline as the sulfonylating reagent, which is highly active, markedly stable, and easily prepared. The scope with respect to the coupling partners – phenols and boronic acids – is broad, and sensitive functional groups are tolerated. Phenols, especially those containing an unprotected amino group, which are generally problematic for coupling under conventional one‐pot conditions, are also viable substrates in this transformation.