Synthesis of γ-Oxo-phosphonates via <i>N</i>-Heterocyclic Carbene-Catalyzed Acylphosphorylation of Alkenes

Mo, Jia-Nan; Sun, Shengbin; Xu, Huiwei; Shu, Hanyu; Zhao, Jiannan

doi:10.1021/acs.orglett.4c00234

Org. Lett.

2024

DOI: 10.1021/acs.orglett.4c00234

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Synthesis of γ-Oxo-phosphonates via N-Heterocyclic Carbene-Catalyzed Acylphosphorylation of Alkenes

Jia-Nan Mo,

Shengbin Sun,

Huiwei Xu

et al.

Abstract: Published as part of Organic Letters virtual special issue "Radical Reactions for the Construction and Transformation of Complex Molecules".

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Cited by 3 publications

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Organocatalytic radical aminoacylation of alkenes for β-aminoketone synthesis

Jialingbieke,

Hu,

Liu

et al. 2024

Sci. China Chem.

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Organocatalytic radical aminoacylation of alkenes for β-aminoketone synthesis

Jialingbieke,

Hu,

Liu

et al. 2024

Sci. China Chem.

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Photocatalytic C(sp³)–P and C(sp²)–P Bond Formation via a Phosphorus Radical Cation

Zhang,

Liu,

et al. 2024

Org. Lett.

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A straightforward method for the phosphorylation of electron-deficient alkenes and aryl alkynes has been developed, leading to C(sp3)–P and C(sp2)–P bond formation. This process involves the generation of phosphorus radical cation intermediates through the photocatalyzed oxidation of ethyl diarylphosphinites. The coupling with electron-deficient alkenes encompasses a variety of heteroaromatics, including pyridine, (benzo)thiazole, and benzoxazole, as well as α,β-unsaturated esters and amides. Impressively, the coupling of radical cations with aryl alkynes demonstrated remarkable regioselectivity, thereby facilitating the synthesis of rare α-aryl vinyl phosphine oxides.

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Copper Mediated sp³-C—N Bond Cleavage for Synthesizing (Diarylmethyl)diarylphosphine Oxides

Dong,

Huo,

Guo

et al. 2024

Chinese Journal of Organic Chemistry

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Synthesis of γ-Oxo-phosphonates via N-Heterocyclic Carbene-Catalyzed Acylphosphorylation of Alkenes

Abstract: Published as part of Organic Letters virtual special issue "Radical Reactions for the Construction and Transformation of Complex Molecules".

Cited by 3 publications

References 69 publications

Organocatalytic radical aminoacylation of alkenes for β-aminoketone synthesis

Organocatalytic radical aminoacylation of alkenes for β-aminoketone synthesis

Photocatalytic C(sp³)–P and C(sp²)–P Bond Formation via a Phosphorus Radical Cation

Copper Mediated sp³-C—N Bond Cleavage for Synthesizing (Diarylmethyl)diarylphosphine Oxides

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Synthesis of γ-Oxo-phosphonates via N-Heterocyclic Carbene-Catalyzed Acylphosphorylation of Alkenes

Abstract: Published as part of Organic Letters virtual special issue "Radical Reactions for the Construction and Transformation of Complex Molecules".

Cited by 3 publications

References 69 publications

Organocatalytic radical aminoacylation of alkenes for β-aminoketone synthesis

Organocatalytic radical aminoacylation of alkenes for β-aminoketone synthesis

Photocatalytic C(sp3)–P and C(sp2)–P Bond Formation via a Phosphorus Radical Cation

Copper Mediated sp3-C—N Bond Cleavage for Synthesizing (Diarylmethyl)diarylphosphine Oxides

Contact Info

Product

Resources

About

Photocatalytic C(sp³)–P and C(sp²)–P Bond Formation via a Phosphorus Radical Cation

Copper Mediated sp³-C—N Bond Cleavage for Synthesizing (Diarylmethyl)diarylphosphine Oxides