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

Nature Communications
Xian ZhaoLingling Chu

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.

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Citations

May 6, 2019·Angewandte Chemie·Yangyang LiGuoyin Yin
Feb 28, 2019·Journal of Physics. Condensed Matter : an Institute of Physics Journal·Y SaleemP Hawrylak
May 23, 2019·Angewandte Chemie·Dirk Leifert, Armido Studer
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May 22, 2020·Angewandte Chemie·Ting LiuCongyang Wang
Jul 8, 2020·Angewandte Chemie·Songlin ZhengWeiming Yuan
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Oct 8, 2019·Journal of the American Chemical Society·Qiao Lin, Tianning Diao
Mar 24, 2020·Organic Letters·Youxiang JinChuan Wang
Apr 20, 2019·Journal of the American Chemical Society·Zhi-Xiong TianXing-Zhong Shu
Jan 24, 2020·Journal of the American Chemical Society·Pei FanChuan Wang
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Jul 1, 2020·Journal of the American Chemical Society·Xiaofeng WeiCristina Nevado
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