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A general copper-catalysed enantioconvergent radical Michaelis–Becker-type C(sp3)–P cross-coupling by Li-Lei Wang; Huan Zhou; Yu-Xi Cao; Chi Zhang; Yang-Qing Ren; Zhong-Liang Li; Qiang-Shuai Gu; Xin-Yuan Liu is a Chemistry article available to read on EtoBox.

What is A general copper-catalysed enantioconvergent radical Michaelis–Becker-type C(sp3)–P cross-coupling about?

The Michaelis–Becker reaction of H-phosphonates with alkyl halides represents an ideal means for synthesizing alkyl phosphorous compounds. However, the enantioconvergent conversion of racemic alkyl halides into α-chiral alkyl phosphorous compounds in this reaction is an insurmountable challenge because of the inherent S N 2 mechanism. Here we disclose a copper-catalysed enantioconvergent radical Michaelis–Becker-type C( sp 3 )–P cross-coupling. Key to the success of this reaction is the use of multidentate chiral anionic ligands for enhancing the reducing capability of the copper catalyst to favour a stereoablative radical pathway over a stereospecific S N 2-type process. Moreover, the ligand architecture is also able to assist the robust association of copper species with alkyl radicals over H-phosphonates, therefore exerting remarkable chemo- and enantioselectivity. This protocol covers a range of (hetero)benzyl-, propargyl- and α-aminocarbonyl alkyl bromides and chlorides. When allied with follow-up transformations, this method provides a versatile platform for valuable α-chiral alkyl phosphorous building blocks and drug leads.

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Author

Li-Lei Wang; Huan Zhou; Yu-Xi Cao; Chi Zhang; Yang-Qing Ren; Zhong-Liang Li; Qiang-Shuai Gu; Xin-Yuan Liu

Publisher

Springer Science and Business Media LLC

Published

2023

Language

EN

Field

Chemistry (Physical Sciences)