Air‐Induced Hydroxyphosphorylation of α‐Trifluoromethyl Styrenes with <i>H</i>‐Phosphonates and <i>H</i>‐Phosphine Oxides

He, Jingjing; Sun, Zhudi; Deng, Yupian; Liu, Ying; Zheng, Pai; Zhang, Xuxue; Cao, Song

doi:10.1002/ejoc.202300719

Eur J Org Chem

2023

DOI: 10.1002/ejoc.202300719

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Air‐Induced Hydroxyphosphorylation of α‐Trifluoromethyl Styrenes with H‐Phosphonates and H‐Phosphine Oxides

Jingjing He,

Zhudi Sun,

Yupian Deng

et al.

Abstract: Efficient synthesis of β‐hydroxy‐β‐CF3‐phosphonates and β‐hydroxy‐β‐CF3‐phosphine oxides by Mn‐mediated or transition‐metal‐free hydroxyphosphorylation of α‐trifluoromethy)styrenes with H‐phosphonates or H‐phosphine oxides with the assistance of air, respectively, was described.

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2024

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Cited by 5 publications

References 66 publications

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Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes

Pan,

Feng,

et al. 2024

Adv Synth Catal

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A visible‐light‐promoted chemodivergent phosphorylation‐peroxidation and oxyphosphorylation of alkenes with phosphine oxides and HOOtBu was realized under transition‐metal‐free conditions. Using the commercially available Eosin Y as a SET‐photocatalyst, the β‐peroxy‐phosphine oxides were selectively obtained with a catalytic amount of base, while the addition of acid led to the exclusive formation of ꞵ‐keto‐phosphine oxides. Control experiments showed that Eosin Y could also act as a HAT‐catalyst to induce the O‐O bond cleavage of peroxides under acidic conditions.

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Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes

Pan,

Feng,

et al. 2024

Adv Synth Catal

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Synthesis of 2‐(β‐Trifluoromethyl‐β‐arylethylthio)pyridine through DBU‐Mediated Regioselective Addition of Pyridine‐2(1H)‐thione Onto α‐(Trifluoromethyl)styrenes

Zheng,

Deng,

et al. 2024

Asian J Org Chem

Self Cite

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An efficient and practical method for the synthesis of (b‐trifluoromethyl‐b‐aryl)ethyl 2‐pyridyl thioethers via hydrothiolation of α‐(trifluoromethyl)styrenes with pyridine‐2(1H)‐thione were reported. The reaction proceeded smoothly and regioselectively in an anti‐Markovnikov manner with the assistance of DBU and afforded a variety of trifluoromethyl‐containing 2‑pyridyl thioethers in moderate to good yields.

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Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF₃ tertiary alcohols

Lu,

Deng,

et al. 2024

Green Chem.

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Air‐Induced Hydroxyphosphorylation of α‐Trifluoromethyl Styrenes with H‐Phosphonates and H‐Phosphine Oxides

Cited by 5 publications

References 66 publications

Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes

Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes

Synthesis of 2‐(β‐Trifluoromethyl‐β‐arylethylthio)pyridine through DBU‐Mediated Regioselective Addition of Pyridine‐2(1H)‐thione Onto α‐(Trifluoromethyl)styrenes

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF₃ tertiary alcohols

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Air‐Induced Hydroxyphosphorylation of α‐Trifluoromethyl Styrenes with H‐Phosphonates and H‐Phosphine Oxides

Cited by 5 publications

References 66 publications

Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes

Photoinduced Transition‐Metal‐Free Chemodivergent Phosphorylation‐Peroxidation and Oxyphosphorylation of Alkenes

Synthesis of 2‐(β‐Trifluoromethyl‐β‐arylethylthio)pyridine through DBU‐Mediated Regioselective Addition of Pyridine‐2(1H)‐thione Onto α‐(Trifluoromethyl)styrenes

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF3 tertiary alcohols

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Product

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Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF₃ tertiary alcohols