Cesium Carbonate-Catalyzed Synthesis of Phosphorothioates via S‑Phosphination of Thioketones

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

doi:10.1039/d2cc04331a

Cesium Carbonate-Catalyzed Synthesis of Phosphorothioates via S‑Phosphination of Thioketones

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

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

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 thioketones were coupled with different phosphite derivatives to provide the corresponding phosphorothioates in good to excellent yields. The control experiments, and density functional theory (DFT) calculations relies on the regio-selective thiophilic addition of phosphite nucleophile via umpolung protocols.

Original language	English (US)
Journal	Chemical Communications
DOIs	https://doi.org/10.1039/d2cc04331a
State	Published - Sep 2 2022

Bibliographical note

KAUST Repository Item: Exported on 2022-09-14
Acknowledgements: This work was financially supported by the Ministry of Science and Technology, Taiwan (Most 110-2113-M-005-014-MY3), National Chung Hsing University, i-Center for Advanced Science and Technology (iCAST), the “Innovation and Development Centre of Sustainable Agriculture (IDCSA)” from The Featured Areas Research Centre Program within the framework of the Higher Education Sprout Project by the Ministry of Education (MOE) in Taiwan and Science and Engineering Research Board-Department of Science. We are also grateful to the service of NOOR 2, Shaheen 2 High Performance Computing Facilities, and financial support from King Abdullah University of Science and Technology (KAUST).

ASJC Scopus subject areas

Materials Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Ceramics and Composites
General Chemistry
Catalysis
Electronic, Optical and Magnetic Materials

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10.1039/d2cc04331a

https://repository.kaust.edu.sa/bitstream/10754/680958/1/d2cc04331a_removed.pdf

Cite this

@article{754c265113bc45118792763c26c5bec1,

title = "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 thioketones were coupled with different phosphite derivatives to provide the corresponding phosphorothioates in good to excellent yields. The control experiments, and density functional theory (DFT) calculations relies on the regio-selective thiophilic addition of phosphite nucleophile via umpolung protocols.",

author = "Ze-Wei Chen and Annamalai Pratheepkumar and Rekha Bai and Yongyi Hu and Badsara, {Satpal Singh} and Kuo-Wei Huang and Chin-Fa Lee",

note = "KAUST Repository Item: Exported on 2022-09-14 Acknowledgements: This work was financially supported by the Ministry of Science and Technology, Taiwan (Most 110-2113-M-005-014-MY3), National Chung Hsing University, i-Center for Advanced Science and Technology (iCAST), the “Innovation and Development Centre of Sustainable Agriculture (IDCSA)” from The Featured Areas Research Centre Program within the framework of the Higher Education Sprout Project by the Ministry of Education (MOE) in Taiwan and Science and Engineering Research Board-Department of Science. We are also grateful to the service of NOOR 2, Shaheen 2 High Performance Computing Facilities, and financial support from King Abdullah University of Science and Technology (KAUST).",

year = "2022",

month = sep,

day = "2",

doi = "10.1039/d2cc04331a",

language = "English (US)",

journal = "Chemical Communications",

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T1 - Cesium Carbonate-Catalyzed Synthesis of Phosphorothioates via S‑Phosphination of Thioketones

AU - Chen, Ze-Wei

AU - Pratheepkumar, Annamalai

AU - Bai, Rekha

AU - Hu, Yongyi

AU - Badsara, Satpal Singh

AU - Huang, Kuo-Wei

AU - Lee, Chin-Fa

N1 - KAUST Repository Item: Exported on 2022-09-14 Acknowledgements: This work was financially supported by the Ministry of Science and Technology, Taiwan (Most 110-2113-M-005-014-MY3), National Chung Hsing University, i-Center for Advanced Science and Technology (iCAST), the “Innovation and Development Centre of Sustainable Agriculture (IDCSA)” from The Featured Areas Research Centre Program within the framework of the Higher Education Sprout Project by the Ministry of Education (MOE) in Taiwan and Science and Engineering Research Board-Department of Science. We are also grateful to the service of NOOR 2, Shaheen 2 High Performance Computing Facilities, and financial support from King Abdullah University of Science and Technology (KAUST).

PY - 2022/9/2

Y1 - 2022/9/2

N2 - 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 thioketones were coupled with different phosphite derivatives to provide the corresponding phosphorothioates in good to excellent yields. The control experiments, and density functional theory (DFT) calculations relies on the regio-selective thiophilic addition of phosphite nucleophile via umpolung protocols.

AB - 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 thioketones were coupled with different phosphite derivatives to provide the corresponding phosphorothioates in good to excellent yields. The control experiments, and density functional theory (DFT) calculations relies on the regio-selective thiophilic addition of phosphite nucleophile via umpolung protocols.

UR - http://hdl.handle.net/10754/680958

UR - http://pubs.rsc.org/en/Content/ArticleLanding/2022/CC/D2CC04331A

U2 - 10.1039/d2cc04331a

DO - 10.1039/d2cc04331a

M3 - Article

C2 - 36093933

SN - 1359-7345

JO - Chemical Communications

JF - Chemical Communications

ER -

Cesium Carbonate-Catalyzed Synthesis of Phosphorothioates via S‑Phosphination of Thioketones

Abstract

Bibliographical note

ASJC Scopus subject areas

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