Organic letters

Cyanocuprates convert carboxylic acids directly into ketones

DT Genna, GH Posner

Index: Genna, Douglas T.; Posner, Gary H. Organic Letters, 2011 , vol. 13, # 19 p. 5358 - 5361

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Citation Number: 25

Abstract

Carboxylic acids were converted directly in 56–99% yields into methyl, n-butyl, and isopropyl ketones using excess cyanocuprates R2CuLi· LiCN. A substrate with a stereocenter α to the carboxylic acid was converted into ketones with very little loss of enantiomeric purity. A variety of functional groups were tolerated including aryl bromides. This direct transformation of a carboxylic acid into ketone with minimal tertiary alcohol ...