NDLI: Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways

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Carboxylates as sources of carbon nucleophiles and electrophiles: comparison of decarboxylative and decarbonylative pathways

Content Provider	Royal Society of Chemistry (RSC)
Author	Dzik, Wojciech I. Gooßen, Lukas J. Lange, Paul P.
Copyright Year	2012
Abstract	This tutorial review provides a comparison between the concepts of catalytic decarboxylative and decarbonylative couplings for the ipso-substitution of carboxylate groups, and illustrates their potential benefits over alternative C–C bond-forming reactions. Redox-neutral decarboxylative reactions allow generating organometallic species with nucleophilic reactivity via the extrusion of carbon dioxide from metal carboxylates. Such C–C bond activating processes provide a way of employing carboxylate salts as substitutes for the traditional sources of carbon nucleophiles, i.e. stoichiometric organometallic reagents. If the decarboxylation of carboxylic acids is performed under oxidative conditions, organometallic species with electrophilic reactivity are obtained instead. These can alternatively be accessed via the extrusion of carbon monoxide from acyl–metal species generated via the oxidative addition of activated carboxylic acid derivatives (e.g. acid chlorides, anhydrides or esters) to metal complexes. In the latter two reaction types, carboxylic acids thus become substitutes for organohalides. The complementary redox-neutral and oxidative decarboxylative and decarbonylative reaction modes allow the broad use of carboxylic acids as substrates in C–C bond-forming reactions. Their applicability, scope and limitations are discussed using the examples of Heck reactions, cross-couplings and direct arylations.
Starting Page	2671
Ending Page	2678
Page Count	8
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	3
Issue Number	9
Journal	Chemical Science
DOI	10.1039/c2sc20312j
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Stoichiometry Oxidative addition Organometallic chemistry Chemical bond Carboxylic acid Decarboxylation Carbon dioxide Arene substitution pattern Carbon monoxide Carbon Nucleophile Electrophile
Content Type	Text
Resource Type	Article
Subject	Chemistry

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