Electrochemical Radical Selenylation of Alkenes and Arenes via Se-Se Bond Activation

Li Sun; Liwei Wang; Hesham Alhumade; Hong Yi; Hu Cai; Aiwen Lei

doi:10.1021/acs.orglett.1c02661

Electrochemical Radical Selenylation of Alkenes and Arenes via Se-Se Bond Activation

Li Sun
, Liwei Wang
, Hesham Alhumade
, Hong Yi^*
, Hu Cai^*
, Aiwen Lei^*

^*Corresponding author for this work

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

76 Scopus citations

Abstract

A novel electrochemical radical selenylation of alkenes and activated arenes without external oxidants is reported. The diselenide was fully transformed into Se-centered radicals through electrochemical Se-Se bond activation. Three-component radical carbonselenation was successfully realized using styrenes to trap the RSe radical. Besides, the direct coupling of RSe radicals with activated arenes was further developed. Using this atom-economic protocol, diversity of unsymmetric aryl-aryl, aryl-alkyl, and alkyl-alkyl selenoethers was obtained regioselectively, which has potential application in biological chemistry.

Original language	English
Pages (from-to)	7724-7729
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	20
DOIs	https://doi.org/10.1021/acs.orglett.1c02661
State	Published - 15 Oct 2021
Externally published	Yes

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Publisher Copyright:
© 2021 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Electrochemical Radical Selenylation of Alkenes and Arenes via Se-Se Bond Activation",

abstract = "A novel electrochemical radical selenylation of alkenes and activated arenes without external oxidants is reported. The diselenide was fully transformed into Se-centered radicals through electrochemical Se-Se bond activation. Three-component radical carbonselenation was successfully realized using styrenes to trap the RSe radical. Besides, the direct coupling of RSe radicals with activated arenes was further developed. Using this atom-economic protocol, diversity of unsymmetric aryl-aryl, aryl-alkyl, and alkyl-alkyl selenoethers was obtained regioselectively, which has potential application in biological chemistry.",

author = "Li Sun and Liwei Wang and Hesham Alhumade and Hong Yi and Hu Cai and Aiwen Lei",

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year = "2021",

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doi = "10.1021/acs.orglett.1c02661",

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T1 - Electrochemical Radical Selenylation of Alkenes and Arenes via Se-Se Bond Activation

AU - Sun, Li

AU - Wang, Liwei

AU - Alhumade, Hesham

AU - Yi, Hong

AU - Cai, Hu

AU - Lei, Aiwen

PY - 2021/10/15

Y1 - 2021/10/15

N2 - A novel electrochemical radical selenylation of alkenes and activated arenes without external oxidants is reported. The diselenide was fully transformed into Se-centered radicals through electrochemical Se-Se bond activation. Three-component radical carbonselenation was successfully realized using styrenes to trap the RSe radical. Besides, the direct coupling of RSe radicals with activated arenes was further developed. Using this atom-economic protocol, diversity of unsymmetric aryl-aryl, aryl-alkyl, and alkyl-alkyl selenoethers was obtained regioselectively, which has potential application in biological chemistry.

AB - A novel electrochemical radical selenylation of alkenes and activated arenes without external oxidants is reported. The diselenide was fully transformed into Se-centered radicals through electrochemical Se-Se bond activation. Three-component radical carbonselenation was successfully realized using styrenes to trap the RSe radical. Besides, the direct coupling of RSe radicals with activated arenes was further developed. Using this atom-economic protocol, diversity of unsymmetric aryl-aryl, aryl-alkyl, and alkyl-alkyl selenoethers was obtained regioselectively, which has potential application in biological chemistry.

UR - https://www.scopus.com/pages/publications/85117091737

U2 - 10.1021/acs.orglett.1c02661

DO - 10.1021/acs.orglett.1c02661

M3 - Article

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AN - SCOPUS:85117091737

SN - 1523-7060

VL - 23

SP - 7724

EP - 7729

JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Electrochemical Radical Selenylation of Alkenes and Arenes via Se-Se Bond Activation

Abstract

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ASJC Scopus subject areas

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