Abstract
Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a vast number of applications for the synthesis of simple building blocks as well as for the functionalization of biologically important skeletons. This review covers the history of carbonylative coupling reactions in Hungary between the years 1994 and 2021.
Highlights
One of the fundamental questions of organic chemistry is the selective formation of new carbon-carbon and carbon-heteroatom bonds [1,2,3]
The goal of this paper is to review all the works on carbonylative coupling reactions reported by Professor Kollár as well as those studies published by researchers working in close collaboration with him in Hungary
In the presence of various primary and secondary amines, such as tert-butylamine and amino acid methyl esters, as N-nucleophiles 2-ketoamides were obtained as major products in aminocarbonylation reaction with formal double carbon monoxide insertion (Figure 9) [47]
Summary
One of the fundamental questions of organic chemistry is the selective formation of new carbon-carbon and carbon-heteroatom bonds [1,2,3]. Mori and co-workers prepared α, β-alkynyl ketones from phenylacetilene and iodoarenes in carbonylative Sonogashira couplings in the presence of copper(I)-iodide, carbon-monoxide and ammonia (c) [9]. A selective example was reported by the Beller-group for a series of carbonylative Negishi reactions aiming at the preparation of 1,2-diaryl-etanones from substituted iodoarenes and benzyl chloride (d) [10]. In the presence of N-nucleophiles, the formation of a new carbon-carbonyl carbonnitrogen bonding pattern is possible and this reaction is usually referred as aminocarbonylation. To the best of our knowledge, the history of carbonylative coupling reactions in Hungary started back in 1994 when Professor László Kollár and Rita Skoda-Földes vinylated steroidal triflates in the absence and in the presence of carbon monoxide [16] (vide infra) at the University of Veszprém (University of Pannonia, since 2006).
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