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. 2015 Jun 26;54(27):7929-33.
doi: 10.1002/anie.201501908. Epub 2015 May 26.

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

Lingling Chu  1 , Jeffrey M Lipshultz  1 , David W C MacMillan  2
Affiliations

Merging Photoredox and Nickel Catalysis: The Direct Synthesis of Ketones by the Decarboxylative Arylation of α-Oxo Acids

Lingling Chu et al. Angew Chem Int Ed Engl. .

Abstract

The direct decarboxylative arylation of α-oxo acids has been achieved by synergistic visible-light-mediated photoredox and nickel catalysis. This method offers rapid entry to aryl and alkyl ketone architectures from simple α-oxo acid precursors via an acyl radical intermediate. Significant substrate scope is observed with respect to both the oxo acid and arene coupling partners. This mild decarboxylative arylation can also be utilized to efficiently access medicinal agents, as demonstrated by the rapid synthesis of fenofibrate.

Keywords: arylation; decarboxylation; nickel catalysis; photoredox catalysis; α-oxo acids.

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Figures

Figure 1
Figure 1
Metallaphotoredox decarboxylative arylation of α-oxo acids.
Scheme 1
Scheme 1
Merged photoredox and nickel catalytic cycles.
Scheme 2
Scheme 2
Metallaphotoredox decarboxylation and its application.
See this image and copyright information in PMC

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