Replacing a stoichiometric silver oxidant with air: ligated Pd( ii )-catalysis to β-aryl carbonyl derivatives with improved chemoselectivity

Air was employed as a green reoxidant of Pd(0), replacing stoichiometric and toxic silver salt, in the chelation-controlled Pd(ii)-modulated arylative enolization of prop-2-en-1-ols to acquire synthetically-important beta -aryl carbonyl derivatives. This green approach, which didn't require aci...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2014-01, Vol.16 (5), p.2788-2797
Main Authors: Vellakkaran, Mari, Andappan, Murugaiah MS, Kommu, Nagaiah
Format: Article
Language:English
Subjects:
Carbonyls
Catalysts
Derivatives
Esters
Labelling
Oxidants
Silver
Toxic
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Summary:Air was employed as a green reoxidant of Pd(0), replacing stoichiometric and toxic silver salt, in the chelation-controlled Pd(ii)-modulated arylative enolization of prop-2-en-1-ols to acquire synthetically-important beta -aryl carbonyl derivatives. This green approach, which didn't require acid or base, allowed the compatibility of a range of functionalities (inclusive of -I, -Br & -Cl), resulting in the construction of structurally-diverse dihydrochalcones, alpha -benzyl- alpha '-alkyl acetones, alpha -benzyl beta -keto esters and dihydrocinnamaldehydes. In addition to organoboronic acids, efficient coupling was also achieved with boronic esters and trifluoroborate salts. A deuterium labelling experiment revealed an interesting 1,2-hydrogen shift after beta -arylation in the catalytic process.
ISSN:1463-9262
1463-9270
DOI:10.1039/c3gc42504e