Catalytic enantioselective reductive domino alkyl arylation of acrylates via nickel/photoredox catalysis

Pengcheng Qian, Haixing Guan, Yan-En Wang, Qianqian Lu, Fan Zhang, Dan Xiong, Patrick J. Walsh () and Jianyou Mao ()
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Pengcheng Qian: Nanjing Tech University
Haixing Guan: Nanjing Tech University
Yan-En Wang: Hebei Agricultural University
Qianqian Lu: Nanjing Tech University
Fan Zhang: Nanjing Tech University
Dan Xiong: Nanjing Tech University
Patrick J. Walsh: University of Pennsylvania
Jianyou Mao: Nanjing Tech University

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract Nonsteroidal anti-inflammatory drug derivatives (NSAIDs) are an important class of medications. Here we show a visible-light-promoted photoredox/nickel catalyzed approach to construct enantioenriched NSAIDs via a three-component alkyl arylation of acrylates. This reductive cross-electrophile coupling avoids preformed organometallic reagents and replaces stoichiometric metal reductants by an organic reductant (Hantzsch ester). A broad range of functional groups are well-tolerated under mild conditions with high enantioselectivities (up to 93% ee) and good yields (up to 90%). A study of the reaction mechanism, as well as literature precedence, enabled a working reaction mechanism to be presented. Key steps include a reduction of the alkyl bromide to the radical, Giese addition of the alkyl radical to the acrylate and capture of the α-carbonyl radical by the enantioenriched nickel catalyst. Reductive elimination from the proposed Ni(III) intermediate generates the product and forms Ni(I).

Date: 2021
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DOI: 10.1038/s41467-021-26794-8

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