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Rhodium‐Catalyzed Decarbonylative Direct Olefination of Arenes with Vinyl Carboxylic Acids
Author(s) -
Qiu Ruiying,
Zhang Lingjuan,
Xu Conghui,
Pan Yixiao,
Pang Hongze,
Xu Lijin,
Li Huanrong
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201401020
Subject(s) - chemistry , rhodium , decarbonylation , catalysis , reagent , organic chemistry , carboxylic acid , combinatorial chemistry
A rhodium(I)‐catalyzed direct CH bond olefination of pyridyl‐substituted arenes with readily available vinyl carboxylic acids has been realized. This reaction occurred efficiently without the need for any external oxidant, affording the ortho ‐olefinated products in high yields and excellent regioselectivities. Diversely substituted vinyl carboxylic acids behaved as efficient olefination reagents under the reaction conditions, and a range of functional groups in both coupling partners was well tolerated. Mechanistic studies indicated that a decarbonylation step is involved in this catalytic process, and pivalic anhydride [( t‐ BuCO) 2 O] acts as the activator of the carboxylic acids for the in situ generation of highly active anhydrides.