Mild Palladium-Catalyzed Oxidative Direct ortho-CH Acylation of Anilides under Aqueous Conditions

Palladium-catalyzed cross-dehydrogenative coupling between anilides and aromatic aldehydes was achieved under aqueous conditions. A wide variety of the desired benzophenone derivatives was isolated in good to excellent yield. The reaction rate acceleration effect of acid and detergent has been demon...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 355; no. 4; pp. 685 - 691
Main Authors Szabo, Fruzsina, Daru, Janos, Simko, Daniel, Nagy, Tibor Zs, Stirling, Andras, Novak, Zoltan
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.03.2013
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
ROOM-TEMPERATURE
ACETANILIDES
O BOND
ORGANIC-REACTIONS
MIYAURA COUPLINGS
acylation
REDUCTIVE ELIMINATION
aldehydes
surfactants
CH activation
CROSS-COUPLINGS
BENZOPHENONE RELATED-COMPOUNDS
H BOND ACYLATION
palladium
ORTHO-ARYLATION
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Summary:Palladium-catalyzed cross-dehydrogenative coupling between anilides and aromatic aldehydes was achieved under aqueous conditions. A wide variety of the desired benzophenone derivatives was isolated in good to excellent yield. The reaction rate acceleration effect of acid and detergent has been demonstrated. Mechanistic insight has been obtained from quantum chemical calculations.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201200948