Synthesis of P-stereogenic cyclicphosphinic amides via electrochemically enabled cobalt-catalyzed enantioselective C–H annulation

The development of an electrochemical process method for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Here, we present an electricity-driven cobalt-catalyzed enantioselective C–H annulation of arylphosphinic amides and alkynes, which provides rapid access to P-chir...

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Veröffentlicht in:Green chemistry : an international journal and green chemistry resource : GC 2023-05, Vol.25 (9), p.3606-3614
Hauptverfasser: Liu, Tao, Zhang, Wangqin, Xu, Chao, Xu, Zhenhui, Song, Dingguo, Qian, Wei, Lu, Gang, Zhang, Chang-Jun, Zhong, Weihui, Ling, Fei
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container_issue 9
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container_title Green chemistry : an international journal and green chemistry resource : GC
container_volume 25
creator Liu, Tao
Zhang, Wangqin
Xu, Chao
Xu, Zhenhui
Song, Dingguo
Qian, Wei
Lu, Gang
Zhang, Chang-Jun
Zhong, Weihui
Ling, Fei
description The development of an electrochemical process method for the synthesis of P-chiral phosphine derivatives poses a considerable challenge. Here, we present an electricity-driven cobalt-catalyzed enantioselective C–H annulation of arylphosphinic amides and alkynes, which provides rapid access to P-chiral cyclicphosphorus oxides in good yields with excellent enantioselectivities (48–99% yields, 94–>99% ee). The reaction was compatible with aqueous solvents and proceeded efficiently in a shorter reaction time compared with the previous work using oxidants. The process employs a combination of readily available chiral salicyloxazoline and cobalt acetate tetrahydrate as an inexpensive catalyst. Notably, the kinetic resolution process was also achieved with s factors up to 347.8. Experimental, kinetic and computational studies on cobalta-electrocatalysis provide insights into the catalyst's working mode.
doi_str_mv 10.1039/D3GC00455D
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Acetic acid
Alkynes
Amides
Catalysts
Chemical reactions
Chemical synthesis
Cobalt
Cobalt acetates
Electrochemistry
Enantiomers
Green chemistry
Organic chemistry
Oxidants
Oxidizing agents
Phosphine
Phosphines
title Synthesis of P-stereogenic cyclicphosphinic amides via electrochemically enabled cobalt-catalyzed enantioselective C–H annulation
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