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Pd/C as a Catalyst for Completely Regioselective CH Functionalization of Thiophenes under Mild Conditions
Author(s) -
Tang DanTam D.,
Collins Karl D.,
Ernst Johannes B.,
Glorius Frank
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201309305
Subject(s) - catalysis , regioselectivity , chemistry , filtration (mathematics) , nitrogen , reaction conditions , functional group , oxygen , surface modification , combinatorial chemistry , medicinal chemistry , organic chemistry , mathematics , polymer , statistics
The completely C3‐selective arylation of thiophenes and benzo[ b ]thiophenes was achieved by using Pd/C as a heterogeneous catalyst without ligands or additives under mild reaction conditions. The practicability of this transformation is demonstrated by notable functional group tolerance and the insensitivity of the reaction to H 2 O and air. This method is also applicable to nitrogen‐ and oxygen‐containing heterocycles, yielding the corresponding C2‐arylated products. Three‐phase tests along with Hg‐poisoning and hot‐filtration tests suggest that the catalytically active species is heterogeneous in nature.