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Palladium‐Catalyzed C2 or C5 Direct Arylation of 3‐Formylthiophene Derivatives with Aryl Bromides
Author(s) -
Dong Jia Jia,
Doucet Henri
Publication year - 2010
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.200901213
Subject(s) - palladium , catalysis , aryl , chemistry , nitrile , nitro , bromide , medicinal chemistry , acetal , combinatorial chemistry , organic chemistry , alkyl
The system Pd(OAc) 2 /dppb was found to be an efficient catalyst precursor for the direct arylation of 3‐formylthiophene derivatives. When using 3‐formylthiophene, the 2‐arylated thiophenes were obtained with regioselectivities of 76–86 %, whereas the arylation of 3‐formylthiophene diethyl acetal gave the 5‐arylated thiophenes with regioselectivities of 64–88 %. These reactions were performed by using only 0.1 mol‐% of the catalyst. Moreover, this procedure has been found to be tolerant to a variety of functional groups on the aryl bromide such as formyl, propionyl, benzoyl, nitrile, or nitro.