Dehydrogenative α,γ-Diphosphinylation\nof Allylamines Enabled by Photoinduced Cobaloxime Catalysis

A regioselective radical α,γ-diphosphinylation\nof allylamines\nwith secondary phosphine oxides by photoinduced cobaloxime catalysis\nis described. The reaction tolerates a wide range of allylamines and\nphosphine oxides, affording α-amino diphosphine dioxides in\nmoderate to good yields with hydrogen evolution. The synthesis of\nnew diphosphine monoxide and diphosphine ligands and the promising\nantitumor activities of products demonstrate the great potential applications\nof this approach in catalysis and drug discovery. The detailed mechanism\nstudies indicate that this reaction likely proceeds through a dehydrogenative\nallylic phosphinylation and nucleophilic addition process.

Publication Details

Journal
Figshare
Published
2024-11-18
DOI
https://doi.org/10.1021/acs.orglett.4c03988.s001
Primary Topic
Organophosphorus compounds synthesis
Type
article
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article

Dehydrogenative α,γ-Diphosphinylation\nof Allylamines Enabled by Photoinduced Cobaloxime Catalysis

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Organophosphorus compounds synthesis
article

Dehydrogenative α,γ-Diphosphinylation\nof Allylamines Enabled by Photoinduced Cobaloxime Catalysis

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Abstract

A regioselective radical α,γ-diphosphinylation\nof allylamines\nwith secondary phosphine oxides by photoinduced cobaloxime catalysis\nis described. The reaction tolerates a wide range of allylamines and\nphosphine oxides, affording α-amino diphosphine dioxides in\nmoderate to good yields with hydrogen evolution. The synthesis of\nnew diphosphine monoxide and diphosphine ligands and the promising\nantitumor activities of products demonstrate the great potential applications\nof this approach in catalysis and drug discovery. The detailed mechanism\nstudies indicate that this reaction likely proceeds through a dehydrogenative\nallylic phosphinylation and nucleophilic addition process.

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Organophosphorus compounds synthesis
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Dehydrogenative α,γ-Diphosphinylation\nof Allylamines Enabled by Photoinduced Cobaloxime Catalysis · Figshare (2024) | TGRS Research Map | TGRS