Cesium carbonate-catalyzed synthesis of phosphorothioates <i>via S</i>-phosphination of thioketones

Chen, Ze-Wei; Annamalai, Pratheepkumar; Bai, Rekha; Hu, Yongyi; Badsara, Satpal Singh; Huang, Kuo‐Wei; Lee, Chin‐Fa

doi:10.1039/d2cc04331a

Chem. Commun.

2022

DOI: 10.1039/d2cc04331a

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Cesium carbonate-catalyzed synthesis of phosphorothioates via S-phosphination of thioketones

Ze-Wei Chen

Pratheepkumar Annamalai

Rekha Bai

et al.

Abstract: A highly efficient and environmentally-friendly base-mediated transition metal-free direct thiophlic catalytic approach has been reported for the synthesis of S-benzhydryl-phosphorothioates by reacting phosphite nucleophiles with diarylmethanethione. A wide variety of...

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2024

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Cited by 4 publications

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Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Peng,

Yang,

et al. 2024

Adv Synth Catal

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Herein, we present a (NH4)2S2O8 mediated difunctionalization reaction of aryl alkenes with quinoxalinones and P(O)SH compounds. This method enables the synthesis of various phosphorothioate‐containing quinoxalin‐2(1H)‐one derivatives (46 examples) in 37‐79% yields. The reaction is compatible with a range of functional groups and is easily adaptable to large‐scale synthesis. Preliminary studies suggest the involvement of phosphorothioate radicals in these transformations.

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Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Peng,

Yang,

et al. 2024

Adv Synth Catal

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Cs₂CO₃-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

López,

Jamis-Oliva,

Lühr

et al. 2024

J. Org. Chem.

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The synthesis of fused benzoxepines relies on the use of complex substrates and methodologies. Herein, we report our experimental and theoretical findings about an unprecedented Rauhut−Currier-type reaction catalyzed by Cs 2 CO 3 to access these important compounds. The developed methodology avoids the use of phosphine-or amine-based catalysts and additives. The reaction can be performed under microwave irradiation and proceeds with complete chemoselectivity.

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Synthesis of mixed phosphorotrithioates via thiol coupling with bis(diisopropylamino)chlorophosphine and sulphenyl chloride

Hussain,

Ahmed,

Padder

et al. 2024

Org. Biomol. Chem.

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Cesium carbonate-catalyzed synthesis of phosphorothioates via S-phosphination of thioketones

Abstract: A highly efficient and environmentally-friendly base-mediated transition metal-free direct thiophlic catalytic approach has been reported for the synthesis of S-benzhydryl-phosphorothioates by reacting phosphite nucleophiles with diarylmethanethione. A wide variety of...

Cited by 4 publications

References 38 publications

Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Cs₂CO₃-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

Synthesis of mixed phosphorotrithioates via thiol coupling with bis(diisopropylamino)chlorophosphine and sulphenyl chloride

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Cesium carbonate-catalyzed synthesis of phosphorothioates via S-phosphination of thioketones

Abstract: A highly efficient and environmentally-friendly base-mediated transition metal-free direct thiophlic catalytic approach has been reported for the synthesis of S-benzhydryl-phosphorothioates by reacting phosphite nucleophiles with diarylmethanethione. A wide variety of...

Cited by 4 publications

References 38 publications

Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Multicomponent Heteroarylphosphorothiolation of Alkenes for Accessing β‐Phosphorothiolated Quinoxalinones

Cs2CO3-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives

Synthesis of mixed phosphorotrithioates via thiol coupling with bis(diisopropylamino)chlorophosphine and sulphenyl chloride

Contact Info

Product

Resources

About

Cs₂CO₃-Catalyzed Rauhut–Currier-Type Reaction for the Synthesis of 2,3-Dihydrobenzo[b]oxepin Derivatives