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Direct Arylation of Thiophenes via Palladium‐Catalysed CH Functionalisation at Low Catalyst Loadings
Author(s) -
Battace Ahmed,
Lemhadri Mhamed,
Zair Touriya,
Doucet Henri,
Santelli Maurice
Publication year - 2007
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.200700142
Subject(s) - chemistry , cyclopentane , aryl , catalysis , thiophene , palladium , trifluoromethyl , steric effects , medicinal chemistry , bromide , nitro , cyclopentanes , nitrile , organic chemistry , alkyl
Palladium associated with cis , cis , cis ‐1,2,3,4 ‐ tetrakis(diphenylphosphinomethyl)cyclopentane (Tedicyp) was found to promote the direct 2‐arylation of a variety of thiophene derivatives via CH functionalisation in good yields using very low catalyst loadings. Electron‐deficient, electron‐excessive or sterically‐congested aryl bromides are tolerated. Moreover, several substituents on the aryl bromide or thiophene derivatives such as acetyl, formyl, nitrile, nitro, ester, methoxy, fluoro or trifluoromethyl are tolerated. The most reactive aryl bromides were coupled with thiophenes derivatives using as little as 0.1–0.01 mol % catalyst.