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Nucleophilic and electrophilic double aroylation of chalcones with benzils promoted by the dimsyl anion as a route to all carbon tetrasubstituted olefins.

Authors :
Ragno D
Bortolini O
Fantin G
Fogagnolo M
Giovannini PP
Massi A
Source :
The Journal of organic chemistry [J Org Chem] 2015 Feb 06; Vol. 80 (3), pp. 1937-45. Date of Electronic Publication: 2015 Jan 09.
Publication Year :
2015

Abstract

Dimsyl anion promoted the polarity reversal of benzils in a Stetter-like reaction with chalcones to give 2-benzoyl-1,4-diones (double aroylation products), which, in turn, were converted into the corresponding tetrasubstituted olefins via aerobic oxidative dehydrogenation catalyzed by Cu(OAc)2.

Details

Language :
English
ISSN :
1520-6904
Volume :
80
Issue :
3
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
25542390
Full Text :
https://doi.org/10.1021/jo502582e