Iron-Catalyzed α-Alkylation of Ketones with Secondary Alcohols: Access to β-Disubstituted Carbonyl Compounds.

Org Lett

Normandie Univ., LCMT, ENSICAEN, UNICAEN, CNRS, 6 boulevard du Maréchal Juin,14000 Caen, France.

Published: March 2020

An iron-catalyzed borrowing hydrogen strategy has been applied in the synthesis of β-branched carbonyl compounds. Various secondary benzylic and aliphatic alcohols have been used as alkylating reagents under mild reaction conditions. The ketones have been isolated in good to excellent yield. Deuterium labeling experiments provide evidence that the alcohol is the hydride source in this reaction and that no reversible step or hydrogen/deuterium scrambling takes place during the process.

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http://dx.doi.org/10.1021/acs.orglett.0c00549DOI Listing

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