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Chapter 14

N-Heterocyclic Carbenes as Organic Catalysts

The synthetic utility of azolium salts as catalysts was thought to be limited to the generation of acyl anion equivalents for use in benzoin and Stetter reactions. The discovery, in 2004, of new catalysts, substrates, and reaction manifolds has ignited a new generation of reactions that fall under the general rubrik of N-heterocyclic carbene (NHC) catalyzed reactions. These powerful new processes include the catalytic generation of activated carboxylates for α-functionalized aldehydes, enantioselective annulations via catalytically generated ester enolate equivalents, and the NHC-catalyzed generation of formal homoenolate equivalents. The history of these new reactions and an overview of the reactions, their substrate scope, and mechanistic pathways are summarized in this Chapter.

Publication details

Print publication date
26 Nov 2010
Copyright year
2011
Print ISBN
978-1-84973-042-6
PDF eISBN
978-1-84973-216-1

From the book series:
Catalysis Series