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Palladium‐Catalyzed α‐Arylation of Carboxylic Acid Derivatives with Grignard Reagent
Author(s) -
Tanaka Daiki,
Tanaka Shota,
Mori Atsunori
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.201402450
Subject(s) - chemistry , deprotonation , palladium , acetic acid , catalysis , aryl , medicinal chemistry , reagent , organic chemistry , yield (engineering) , halide , carboxylic acid , bromide , ion , alkyl , materials science , metallurgy
The reaction of arylacetic acid with aryl halides in the presence of a palladium(0) catalyst proceeds with a Grignard reagent (2 equiv.) to afford diarylated acetic acids. Deprotonation was confirmed by treatment with allyl bromide, which revealed that the use of EtMgCl or t BuMgCl at room temperature to 60 °C resulted in complete deprotonation. After deprotonation of (4‐methoxyphenyl)acetic acid under such conditions, the resulting mixture was treated with 4‐methoxybromobenzene in the presence of Pd( t Bu 3 P) 2 (2 mol‐%) as a catalyst to give bis(4‐methoxyphenyl)acetic acid in 86 % yield. The reaction with several aryl halides under similar conditions gave the corresponding diarylacetic acids.