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A New Route to Phenols: Palladium‐Catalyzed Cyclization and Oxidation of γ,δ‐Unsaturated Ketones
Author(s) -
Samadi Sadaf,
Orellana Arturo
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600447
Subject(s) - palladium , cyclohexanone , phenols , enol , chemistry , phenol , catalysis , ketone , alkene , organic chemistry , substrate (aquarium) , combinatorial chemistry , oceanography , geology
We report a new strategy for the synthesis of phenols from acyclic unsaturated ketones in one pot. The reaction proceeds by palladium‐catalyzed carbopalladation of an alkene with the enol form of the tethered ketone, generating a substituted cyclohexanone. Upon introduction of a terminal oxidant a palladium‐catalyzed oxidation ensues to give the desired phenol. This approach allows the programming of phenol substituents on the acyclic substrate and therefore circumvents the limitations inherent in traditional syntheses of phenols.