the Carboxylic Acids directly into the Ketones;
Cyanocuprates Convert Carboxylic Acids Directly into Ketones
Department of Chemistry,
School of Arts and Sciences, The Johns Hopkins University,
3400 North Charles Street, Baltimore, Maryland 21218-2685, United States
Org. Lett., 2011, 13 (19), pp 5358–5361
DOI: 10.1021/ol202237j
Publication Date (Web): September 6, 2011
Copyright © 2011 American Chemical Society
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 formation is proposed to involve a relatively stable copper ketal tetrahedral intermediate.
Supporting Information
1H and 13C NMR spectra for all new compounds. This material is available free of charge via the Internet at http://pubs.acs.org.
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