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Palladium‐catalyzed selective decarboxylative coupling reaction versus direct C―H arylation for arylation of heteroaromatics
Author(s) -
Fu Haiyan,
Chen Hua,
Doucet Henri
Publication year - 2013
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3037
Subject(s) - chemistry , palladium , catalysis , aryl , nitro , furan , nitrile , phosphine , thiophene , decarboxylation , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl
Conditions for selective palladium‐catalyzed decarboxylative 2‐arylation of 3‐substituted thiophene and furan derivatives bearing an ester at C2 position have been established. By using 2 mol% phosphine‐free Pd(OAc) 2 as the catalyst and a mixture of KOH and K 2 CO 3 as the bases, in dimethylacetamide, moderate to good yields of the desired 2‐arylated products were obtained. A range of functional groups such as nitrile, nitro, formyl or acetyl on the aryl bromides was tolerated. This method allows us to employ in some cases more convenient reactants in terms of cost or physical properties (boiling point) for arylations . Copyright © 2013 John Wiley & Sons, Ltd.