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Palladium‐Catalyzed C(sp 2 )−H Alkylation of Aldehyde‐Derived Hydrazones with Functionalized Difluoromethyl Bromides
Author(s) -
Prieto Alexis,
Melot Romain,
Bouyssi Didier,
Monteiro Nuno
Publication year - 2016
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.201510334
Subject(s) - aldehyde , palladium , chemistry , catalysis , alkylation , catalytic cycle , hydrazone , combinatorial chemistry , medicinal chemistry , organic chemistry
A palladium‐catalyzed C(sp 2 )−H difluoromethylation of aldehyde‐derived hydrazones using bromodifluoromethylated compounds to afford the corresponding functionalized difluoromethylketone hydrazones has been established. It is proposed that a radical/SET mechanism proceeding via a difluoroalkyl radical may be involved in the catalytic cycle. Applications of the methodology to the synthesis of α,α‐difluoro‐β‐ketoesters and α,α‐difluoroketones (RCOCF 2 H) have been illustrated.