Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay

Xian Zhao, Hai-Yong Tu, Lei Guo, Shengqing Zhu, Feng-Ling Qing and Lingling Chu ()
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Xian Zhao: Donghua University
Hai-Yong Tu: Donghua University
Lei Guo: Donghua University
Shengqing Zhu: Donghua University
Feng-Ling Qing: Donghua University
Lingling Chu: Donghua University

Nature Communications, 2018, vol. 9, issue 1, 1-7

Abstract: Abstract The development of catalytic carboacylation of simple olefins, which would enable the rapid construction of ketones with high levels of complexity and diversity, is very challenging. To date, the vast majority of alkene carboacylation reactions are typically restricted to single- and two-component methodologies. Here we describe a three-component carboacylation of alkenes via the merger of radical chemistry with nickel catalysis. This reaction manifold utilizes a radical relay strategy involving radical addition to an alkene followed by alkyl radical capture by an acyl-nickel complex to forge two vicinal C−C bonds under mild conditions. Excellent chemoselectivity and regioselectivity have been achieved by utilizing a pendant weakly chelating group. This versatile protocol allows for facile access to a wide range of important β-fluoroalkyl ketones from simple starting materials.

Date: 2018
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DOI: 10.1038/s41467-018-05951-6

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