Selective C(sp<sup>2</sup>)–P Cross-Couplingof Alkenylsulfonium Salts with P(O)H Compounds: Divergent Synthesisof Alkenylphosphorus Compounds

Herein, we report a both regioselective and stereoselective method for the formation of C(sp<sup>2</sup>)–P bonds using alkenylsulfonium salts and >P(O)–H compounds. By employing a palladium catalyst or K<sub>2</sub>CO<sub>3</sub>, a variety of (<i>E</i>)-alkenylphosphorus compounds and terminal alkenylphosphorus compounds were successfully synthesized with high selectivity. Notably, trisubstituted (<i>Z</i>)-alkenylphosphorus compounds were synthesized for the first time under metal-free conditions. This protocol has a wide substrate scope and good functional group compatibility, providing a direct and highly selective approach for the preparation of various alkenylphosphorus compounds.

Publication Details

Journal
Figshare
Published
2025-03-13
DOI
https://doi.org/10.1021/acs.orglett.5c00318.s001
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Selective C(sp2)–P Cross-Couplingof Alkenylsulfonium Salts with P(O)H Compounds: Divergent Synthesisof Alkenylphosphorus Compounds

Figshare
Sulfur-Based Synthesis Techniques
article

Selective C(sp2)–P Cross-Couplingof Alkenylsulfonium Salts with P(O)H Compounds: Divergent Synthesisof Alkenylphosphorus Compounds

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Abstract

Herein, we report a both regioselective and stereoselective method for the formation of C(sp<sup>2</sup>)–P bonds using alkenylsulfonium salts and >P(O)–H compounds. By employing a palladium catalyst or K<sub>2</sub>CO<sub>3</sub>, a variety of (<i>E</i>)-alkenylphosphorus compounds and terminal alkenylphosphorus compounds were successfully synthesized with high selectivity. Notably, trisubstituted (<i>Z</i>)-alkenylphosphorus compounds were synthesized for the first time under metal-free conditions. This protocol has a wide substrate scope and good functional group compatibility, providing a direct and highly selective approach for the preparation of various alkenylphosphorus compounds.

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Sulfur-Based Synthesis Techniques
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Selective C(sp<sup>2</sup>)–P Cross-Couplingof Alkenylsulfonium Salts with P(O)H Compounds: Divergent Synthesisof Alkenylphosphorus Compounds · Figshare (2025) | TGRS Research Map | TGRS