Regio‐ and Diastereoselective KMnO4/RCO2H Mediated Acyloxyarylation of Chalcones – An Indirect α‐Arylation of Chalcones

A MnVII‐mediated regio‐ and diastereoselective acyloxyarylation of chalcones is unveiled. Heating a solution of a chalcone and an arylboronic acid in an aliphatic carboxylic acid at 80 °C for 1 h afforded the corresponding 1‐acyloxy‐3‐oxo‐1,2,3‐triarylpropanes in high yields. The β‐acyloxy‐α‐arylati...

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Bibliographic Details
Published in:European journal of organic chemistry 2020-04, Vol.2020 (14), p.2045-2051
Main Authors: Adib, Mehdi, Rajai‐Daryasarei, Saideh, Pashazadeh, Rahim, Mahdavi, Mohammad, Madadi, Mozhdeh, Jahani, Mehdi
Format: Article
Language:English
Subjects:
Aliphatic compounds
Arylation
Carboxylic acids
Chalcones
Diastereoselectivity
Potassium permanganate
Reaction mechanisms
Regioselectivity
Stereoselectivity
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Summary:A MnVII‐mediated regio‐ and diastereoselective acyloxyarylation of chalcones is unveiled. Heating a solution of a chalcone and an arylboronic acid in an aliphatic carboxylic acid at 80 °C for 1 h afforded the corresponding 1‐acyloxy‐3‐oxo‐1,2,3‐triarylpropanes in high yields. The β‐acyloxy‐α‐arylation/elimination sequence can be regarded as an indirect α‐arylation of chalcones. A manganese(VII)‐mediated regio‐ and diastereoselective acyloxyarylation of chalcones is unveiled. Heating a solution of a chalcone and an arylboronic acid in an aliphatic carboxylic acid at 80 °C for 1 h afforded the corresponding 1‐acyloxy‐3‐oxo‐1,2,3‐triarylpropanes in high yields. The β‐acyloxy‐α‐arylation/elimination sequence can be regarded as an indirect α‐arylation of chalcones.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201901647