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Palladium‐Catalyzed Oxidative CC Bond Cleavage of α‐Hydroxyketones: Application to CH Acylation of Azoarenes and Synthesis of a Liver(X) Receptor Agonist
Author(s) -
Majhi Biju,
Ahammed Sabir,
Kundu Debasish,
Ranu Brindaban C.
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402280
Subject(s) - chemistry , acylation , moiety , palladium , regioselectivity , agonist , catalysis , bond cleavage , oxidative phosphorylation , cleavage (geology) , medicinal chemistry , hydrogen peroxide , stereochemistry , organic chemistry , receptor , biochemistry , geotechnical engineering , fracture (geology) , engineering
Palladium‐catalyzed oxidative CC cleavage of α‐hydroxyketones and 2‐aryl acetophenones in the presence of tert ‐butyl hydrogen peroxide (TBHP) generates an acyl moiety, which promotes subsequent regioselective CH acylation producing a series of ortho‐ acyl substituted symmetrical and unsymmetrical azoarenes. This protocol is successfully used for the synthesis of liver (X) receptor agonist.