Oxidative Thioesterification of Alkenes Mediated by 1,3-Dibromo-5,5-dimethylhydantoin and DMSO for the Synthesis of α-Ketothioesters

Jiawei Hua; Jiaqi Xu; Jia Xu; Bochao Zhou; Dong Zhang; Zhao Yang; Zheng Fang; Kai Guo

doi:10.1002/ejoc.201900585

Oxidative Thioesterification of Alkenes Mediated by 1,3-Dibromo-5,5-dimethylhydantoin and DMSO for the Synthesis of α-Ketothioesters

Jiawei Hua, Jiaqi Xu, Jia Xu, Bochao Zhou, Dong Zhang, Zhao Yang, Zheng Fang, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

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

10 Scopus citations

Abstract

A simple and mild approach for the synthesis of α-ketothioesters via 1,3-Dibromo-5,5-dimethylhydantoin (DBH)/DMSO mediated oxidative thioesterification of alkenes has been developed. Various of α-ketothioesters products were produced in moderate to good yields under metal-free conditions. And this method features readily available starting materials and broad substrate scope. Moreover, a plausible mechanism was proposed based on the methyl bromide captured experiment.

Original language	English
Pages (from-to)	4056-4060
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.201900585
State	Published - 7 Jul 2019

Keywords

Alkenes
Oxidation
Synthetic methods
Thioesters

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10.1002/ejoc.201900585

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title = "Oxidative Thioesterification of Alkenes Mediated by 1,3-Dibromo-5,5-dimethylhydantoin and DMSO for the Synthesis of α-Ketothioesters",

abstract = "A simple and mild approach for the synthesis of α-ketothioesters via 1,3-Dibromo-5,5-dimethylhydantoin (DBH)/DMSO mediated oxidative thioesterification of alkenes has been developed. Various of α-ketothioesters products were produced in moderate to good yields under metal-free conditions. And this method features readily available starting materials and broad substrate scope. Moreover, a plausible mechanism was proposed based on the methyl bromide captured experiment.",

keywords = "Alkenes, Oxidation, Synthetic methods, Thioesters",

author = "Jiawei Hua and Jiaqi Xu and Jia Xu and Bochao Zhou and Dong Zhang and Zhao Yang and Zheng Fang and Kai Guo",

note = "Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2019",

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doi = "10.1002/ejoc.201900585",

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T1 - Oxidative Thioesterification of Alkenes Mediated by 1,3-Dibromo-5,5-dimethylhydantoin and DMSO for the Synthesis of α-Ketothioesters

AU - Hua, Jiawei

AU - Xu, Jiaqi

AU - Xu, Jia

AU - Zhou, Bochao

AU - Zhang, Dong

AU - Yang, Zhao

AU - Fang, Zheng

AU - Guo, Kai

PY - 2019/7/7

Y1 - 2019/7/7

N2 - A simple and mild approach for the synthesis of α-ketothioesters via 1,3-Dibromo-5,5-dimethylhydantoin (DBH)/DMSO mediated oxidative thioesterification of alkenes has been developed. Various of α-ketothioesters products were produced in moderate to good yields under metal-free conditions. And this method features readily available starting materials and broad substrate scope. Moreover, a plausible mechanism was proposed based on the methyl bromide captured experiment.

AB - A simple and mild approach for the synthesis of α-ketothioesters via 1,3-Dibromo-5,5-dimethylhydantoin (DBH)/DMSO mediated oxidative thioesterification of alkenes has been developed. Various of α-ketothioesters products were produced in moderate to good yields under metal-free conditions. And this method features readily available starting materials and broad substrate scope. Moreover, a plausible mechanism was proposed based on the methyl bromide captured experiment.

KW - Alkenes

KW - Oxidation

KW - Synthetic methods

KW - Thioesters

UR - http://www.scopus.com/inward/record.url?scp=85068028250&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201900585

DO - 10.1002/ejoc.201900585

M3 - 文章

AN - SCOPUS:85068028250

SN - 1434-193X

VL - 2019

SP - 4056

EP - 4060

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

ER -

Oxidative Thioesterification of Alkenes Mediated by 1,3-Dibromo-5,5-dimethylhydantoin and DMSO for the Synthesis of α-Ketothioesters

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Keywords

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