Direct Conversion of Carboxylic Acids to Alkyl Ketones

An efficient and mild method for acyl–Csp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated carboxylic acids and alkyltrifluoroborates. This versatil...

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Bibliographic Details
Published in:Organic letters 2017-07, Vol.19 (13), p.3612-3615
Main Authors: Amani, Javad, Molander, Gary A
Format: Article
Language:English
Subjects:
carboxylic acids
chemical structure
cross-coupling reactions
ketones
Letter
potassium
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Summary:An efficient and mild method for acyl–Csp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated carboxylic acids and alkyltrifluoroborates. This versatile method is amenable to the cross-coupling of structurally diverse carboxylic acids with various potassium alkyltrifluoroborates, affording the corresponding ketones with high yields. In this operationally simple cross-coupling protocol, aliphatic ketones are obtained in one step from bench stable, readily available carboxylic acids.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.7b01588