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. 2017 Jul 7;19(13):3612-3615.
doi: 10.1021/acs.orglett.7b01588. Epub 2017 Jun 12.

Direct Conversion of Carboxylic Acids to Alkyl Ketones

Javad Amani  1 , Gary A Molander  1
Affiliations

Direct Conversion of Carboxylic Acids to Alkyl Ketones

Javad Amani et al. Org Lett. .

Abstract

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.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Photoredox/Ni dual catalysis cross-coupling of carboxylic acids with alkyltrifluoroborates.
Figure 2
Figure 2
Proposed mechanism for the acyl-sp3 cross-coupling.
Scheme 1
Scheme 1. Scope of Potassium Alkyltrifluoroborates in Cross-Coupling with Carboxylic Acids
See Supporting Information for experimental details. All cited yields are isolated. Reaction performed on 7.0 mmol scale with 1.5 mol % of Ir photocatalyst 1 and 3.0 mol % of [Ni(dtbbpy)(H2O)4]Cl2.
See this image and copyright information in PMC

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