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Synlett 2014; 25(07): 911-919
DOI: 10.1055/s-0033-1340174
DOI: 10.1055/s-0033-1340174
account
Palladium-Catalyzed Decarboxylative Cross-Coupling of α-Oxocarboxylic Acids and Their Derivatives
Further Information
Publication History
Received: 29 August 2013
Accepted after revision: 10 December 2013
Publication Date:
31 January 2014 (online)
Abstract
The development of palladium(II)-catalyzed decarboxylative cross-coupling of α-oxocarboxylic acids and their derivatives is summarized in this account. Acetanilides, 2-phenyl-pyridines, and benzoic acids were found to be suitable substrates for direct acylation through decarboxylative cross-coupling with α-oxocarboxylic acids. Potassium aryl trifluoroborates were also transformed into ketones, amides, and esters with α-oxocarboxylic acids, oxamic acids, and oxalate monoesters, respectively, in modified catalytic systems.
1 Introduction
2 Palladium-Catalyzed Decarboxylative Cross-Coupling Through C–H Bond Functionalization
2.1 Direct ortho-Acylation of Acetanilides
2.2 Direct Acylation of 2-Phenylpyridines
2.3 Direct ortho-Acylation of Benzoic Acids
3 Transformation of Potassium Aryl Trifluoroborates into Ketones, Esters, and Amides
3.1 Formation of Aryl Ketones from Potassium Aryl Trifluoroborates
3.2 Preparation of Aryl Amides and Esters from Potassium Aryl Trifluoroborates
3.3 Mechanistic Studies
4 Conclusions and Outlook
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