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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Cross Redox Coupling of Aryl-Aldehydes and p-Benzoquinone
1School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar ; Institute of Physics Campus, P.O. Sainik School; Bhubaneswar, Odisha 751 005, India.
Abstract:
Herein, we report an unprecedented Cross Redox Coupling (CRC) reaction catalyzed by Cu(OAc)2·H2O. As a proof-of-concept, direct coupling of aromatic aldehydes (or alcohols) and p-benzoquinone led to an ester in the presence of the Cu(II)-TBHP combination. During the coupling process, the C-H bond of the aldehydes was converted directly to a C-O bond. Mechanistically, we propose that the reaction proceeded via a radical pathway. In addition, atom and electron economies were well-conserved during this CRC reaction.
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