Selective Functionalization\nof White Phosphorus with\nAlkyl Bromides under Photocatalytic Conditions: A Chlorine-Free Protocol\nto Dialkyl and Trialkyl Phosphine Oxides

A novel and efficient method for the direct selective\nalkylation\nof white phosphorus (P<sub>4</sub>) with alkyl bromides has been developed,\nutilizing 4DPAIPN as the photocatalyst and Hantzsch ester as the reductant.\nThis method facilitates the synthesis of structurally diverse dialkyl\nphosphine oxides in good yields, offering a streamlined alternative\nto the traditional stepwise approach of chlorinating P<sub>4</sub> with Cl<sub>2</sub> and subsequently displacing the chlorine atom.\nNoteworthy features of this reaction include excellent product selectivity,\nremarkable functional group tolerance, and a broad substrate scope.\nAdditionally, this method is effective for the synthesis of trialkyl\nphosphine oxides.

Publication Details

Journal
Figshare
Published
2024-10-24
DOI
https://doi.org/10.1021/acs.orglett.4c03494.s001
Primary Topic
Organophosphorus compounds synthesis
Type
article
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article

Selective Functionalization\nof White Phosphorus with\nAlkyl Bromides under Photocatalytic Conditions: A Chlorine-Free Protocol\nto Dialkyl and Trialkyl Phosphine Oxides

Figshare
Organophosphorus compounds synthesis
article

Selective Functionalization\nof White Phosphorus with\nAlkyl Bromides under Photocatalytic Conditions: A Chlorine-Free Protocol\nto Dialkyl and Trialkyl Phosphine Oxides

article en

Abstract

A novel and efficient method for the direct selective\nalkylation\nof white phosphorus (P<sub>4</sub>) with alkyl bromides has been developed,\nutilizing 4DPAIPN as the photocatalyst and Hantzsch ester as the reductant.\nThis method facilitates the synthesis of structurally diverse dialkyl\nphosphine oxides in good yields, offering a streamlined alternative\nto the traditional stepwise approach of chlorinating P<sub>4</sub> with Cl<sub>2</sub> and subsequently displacing the chlorine atom.\nNoteworthy features of this reaction include excellent product selectivity,\nremarkable functional group tolerance, and a broad substrate scope.\nAdditionally, this method is effective for the synthesis of trialkyl\nphosphine oxides.

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Openalex Percentile: Top 76%
Organophosphorus compounds synthesis
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