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Switching the Regioselectivity of Direct C–H Arylation of 1,3‐Dimethyluracil
Author(s) -
Čerňová Miroslava,
Pohl Radek,
Hocek Michal
Publication year - 2009
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.200900586
Subject(s) - regioselectivity , chemistry , aryl , halide , catalysis , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
An interesting dichotomy in the regioselectivity and mechanism of direct C–H arylation of 1,3‐dimethyluracil was observed. Its Pd‐catalyzed reactions with diverse aryl halides in the absence of CuI lead preferentially to 5‐aryluracils, while reactions in the presence of CuI give 6‐aryl derivatives as the major products. Cu‐mediated reactions (in the absence of a Pd catalyst) proceed with lower efficiency but give exclusively 6‐aryluracil derivatives. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)