Photocatalytic EnT-Mediated Aminophosphorylation of\nAlkenes Using Oxime Esters as Bifunctional Reagents

C–P\nbond formation has typically been achieved by a single-electron\ntransfer process. Herein, a novel class of oxime ester bifunctionalization\nreagents were first applied to the photocatalytic β-aminophosphorylation\nof modular olefins. The bifunctional reagents generate two distinct\nradical species (imine and phosphoryl radicals) that exhibit excellent\nregioselectivity. Subsequently, these radicals are attached to the\nolefins through a single-step EnT catalytic process, establishing\na novel synthetic pathway. This protocol is characterized by excellent\nregioselectivity, broad functional group tolerance, and mild reaction\nconditions, which would enrich the diversity and versatility to facilitate\nthe diversity-oriented synthesis of β-aminophosphorylated complex\nmolecule scaffolds.

Publication Details

Journal
Figshare
Published
2024-11-19
DOI
https://doi.org/10.1021/acs.orglett.4c03790.s001
Primary Topic
Organophosphorus compounds synthesis
Type
article
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article

Photocatalytic EnT-Mediated Aminophosphorylation of\nAlkenes Using Oxime Esters as Bifunctional Reagents

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Organophosphorus compounds synthesis
article

Photocatalytic EnT-Mediated Aminophosphorylation of\nAlkenes Using Oxime Esters as Bifunctional Reagents

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Abstract

C–P\nbond formation has typically been achieved by a single-electron\ntransfer process. Herein, a novel class of oxime ester bifunctionalization\nreagents were first applied to the photocatalytic β-aminophosphorylation\nof modular olefins. The bifunctional reagents generate two distinct\nradical species (imine and phosphoryl radicals) that exhibit excellent\nregioselectivity. Subsequently, these radicals are attached to the\nolefins through a single-step EnT catalytic process, establishing\na novel synthetic pathway. This protocol is characterized by excellent\nregioselectivity, broad functional group tolerance, and mild reaction\nconditions, which would enrich the diversity and versatility to facilitate\nthe diversity-oriented synthesis of β-aminophosphorylated complex\nmolecule scaffolds.

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Organophosphorus compounds synthesis
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