N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes

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منابع مشابه

N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes† †Electronic supplementary information (ESI) available: Experimental procedures and 1H and 13C NMR of new materials. See DOI: 10.1039/c4sc03726j Click here for additional data file.

N-Heterocyclic carbene catalysed redox isomerisation with reduction about the carbonyl has been developed in the transformation of trienyl esters to tetrasubstituted benzaldehydes. The reaction proceeds in good to excellent yield, and in cases that provide 2,20-biaryls, enantioselectivity is observed. Mechanistic studies demonstrate the intermediacy of a cyclohexenyl b-lactone, while implicatin...

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N-heterocyclic carbene catalysed aerobic oxidation of aromatic aldehydes to aryl esters using boronic acids.

The organocatalytic behavior of N-heterocyclic carbenes in the aerobic oxidation of aromatic aldehydes to esters with boronic acids has been explored. This transition metal-free protocol allows access to a wide variety of aromatic esters in good to excellent yields under mild reaction conditions.

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N-heterocyclic carbene-catalysed intermolecular Stetter reactions of acetaldehyde.

A facile method for the intermolecular Stetter reaction of various Michael acceptors with acetaldehyde as a biomimetic acylanion source was realized using N-heterocyclic carbene catalysis. This catalytic system has also been applied to the enantioselective Stetter reaction and resulted in moderate to good enantioselectivities for the corresponding Stetter products.

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Recent advances in N-heterocyclic carbene (NHC)-catalysed benzoin reactions

N-Heterocyclic carbenes (NHCs) have emerged as a powerful class of organocatalysts that mediate a variety of organic transformations. The Benzoin reaction constitutes one of the earliest known carbon-carbon bond-forming reactions catalysed by NHCs. The rapid growth of NHC catalysis in general has resulted in the development of a variety of benzoin and benzoin-type reactions. An overview of such...

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A triazolium salt derived N-heterocyclic carbene catalyzes the redox esterification reaction between α-β-unsaturated aldehydes and oximes. The resulting saturated oxime esters were obtained in very good yields for a broad range of aliphatic, aromatic and heteroaromatic substrates.

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ژورنال

عنوان ژورنال: Chemical Science

سال: 2015

ISSN: 2041-6520,2041-6539

DOI: 10.1039/c4sc03726j