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J Am Chem Soc. 2019 Mar 6;141(9):3854-3858. doi: 10.1021/jacs.9b00880. Epub 2019 Feb 22.

N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes.

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1
Division of Pharmaceutical Sciences, Graduate School of Medical Sciences , Kanazawa University , Kakuma-machi, Kanazawa 920-1192 , Japan.

Abstract

We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.

PMID:
30785739
DOI:
10.1021/jacs.9b00880

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