Peroxide- And transition metal-free electrochemical synthesis of α,β-epoxy ketones

Mengxun Zhang; Tie Chen; Shisong Fang; Weihua Wu; Xin Wang; Haiqiang Wu; Yongai Xiong; Jun Song; Chenyang Li; Zhendan He; Chi Sing Lee

doi:10.1039/d0ob02444a

Peroxide- And transition metal-free electrochemical synthesis of α,β-epoxy ketones

Mengxun Zhang
, Tie Chen
, Shisong Fang
, Weihua Wu
, Xin Wang
, Haiqiang Wu
, Yongai Xiong
, Jun Song
, Chenyang Li^*
, Zhendan He^*
, Chi Sing Lee^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

7 Citations (Scopus)

Abstract

A novel electrochemical method for the synthesis of α,β-epoxy ketones is reported. With KI as the redox mediator, methyl ketones reacted with aldehydes under peroxide- and transition metal-free electrolytic conditions and afforded α,β-epoxy ketones in one pot (36 examples, 52-90% yield). This safe and environmental-friendly method has a broad substrate scope and can readily provide a variety of α,β-epoxy ketones in gram-scales for evaluation of their anti-cancer activities.

Original language	English
Pages (from-to)	2481-2486
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	19
Issue number	11
Early online date	26 Feb 2021
DOIs	https://doi.org/10.1039/d0ob02444a
Publication status	Published - 21 Mar 2021

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10.1039/d0ob02444a

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@article{79a741d835324ed8ba9d55a6f9281ac2,

title = "Peroxide- And transition metal-free electrochemical synthesis of α,β-epoxy ketones",

abstract = "A novel electrochemical method for the synthesis of α,β-epoxy ketones is reported. With KI as the redox mediator, methyl ketones reacted with aldehydes under peroxide- and transition metal-free electrolytic conditions and afforded α,β-epoxy ketones in one pot (36 examples, 52-90\% yield). This safe and environmental-friendly method has a broad substrate scope and can readily provide a variety of α,β-epoxy ketones in gram-scales for evaluation of their anti-cancer activities.",

author = "Mengxun Zhang and Tie Chen and Shisong Fang and Weihua Wu and Xin Wang and Haiqiang Wu and Yongai Xiong and Jun Song and Chenyang Li and Zhendan He and Lee, \{Chi Sing\}",

note = "Funding Information: This work was financially supported by the National Key R \& D Program of China 2017YFA0503900, the National Natural Science Foundation of China (31670360, 81973293, U1702286 and 81871631), the Shenzhen Science and Technology Innovation Committee Grant (ZDSYS201506031617582 and JCYJ20190808122213241) and the Natural Science Foundation of Guangdong Province, China (2019B1515120029 and 2017B030301016). A special acknowledgement is made to Instrumental Analysis Center of Shenzhen University for their instruments and service.",

year = "2021",

month = mar,

day = "21",

doi = "10.1039/d0ob02444a",

language = "English",

volume = "19",

pages = "2481--2486",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "11",

}

TY - JOUR

T1 - Peroxide- And transition metal-free electrochemical synthesis of α,β-epoxy ketones

AU - Zhang, Mengxun

AU - Chen, Tie

AU - Fang, Shisong

AU - Wu, Weihua

AU - Wang, Xin

AU - Wu, Haiqiang

AU - Xiong, Yongai

AU - Song, Jun

AU - Li, Chenyang

AU - He, Zhendan

AU - Lee, Chi Sing

N1 - Funding Information: This work was financially supported by the National Key R & D Program of China 2017YFA0503900, the National Natural Science Foundation of China (31670360, 81973293, U1702286 and 81871631), the Shenzhen Science and Technology Innovation Committee Grant (ZDSYS201506031617582 and JCYJ20190808122213241) and the Natural Science Foundation of Guangdong Province, China (2019B1515120029 and 2017B030301016). A special acknowledgement is made to Instrumental Analysis Center of Shenzhen University for their instruments and service.

PY - 2021/3/21

Y1 - 2021/3/21

N2 - A novel electrochemical method for the synthesis of α,β-epoxy ketones is reported. With KI as the redox mediator, methyl ketones reacted with aldehydes under peroxide- and transition metal-free electrolytic conditions and afforded α,β-epoxy ketones in one pot (36 examples, 52-90% yield). This safe and environmental-friendly method has a broad substrate scope and can readily provide a variety of α,β-epoxy ketones in gram-scales for evaluation of their anti-cancer activities.

AB - A novel electrochemical method for the synthesis of α,β-epoxy ketones is reported. With KI as the redox mediator, methyl ketones reacted with aldehydes under peroxide- and transition metal-free electrolytic conditions and afforded α,β-epoxy ketones in one pot (36 examples, 52-90% yield). This safe and environmental-friendly method has a broad substrate scope and can readily provide a variety of α,β-epoxy ketones in gram-scales for evaluation of their anti-cancer activities.

UR - https://www.scopus.com/pages/publications/85103242896

U2 - 10.1039/d0ob02444a

DO - 10.1039/d0ob02444a

M3 - Journal article

C2 - 33656035

AN - SCOPUS:85103242896

SN - 1477-0520

VL - 19

SP - 2481

EP - 2486

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 11

ER -

Peroxide- And transition metal-free electrochemical synthesis of α,β-epoxy ketones

Abstract

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