Synthesis of β-Hydroxy Aryl Selenides via Transition-Metal-Free Three-Component Reaction of Arylamines, Elemental Selenium, and Epoxides

Hongwei Wang; Hongchen Li; Yalong Bai; Yanling Hei; Junwei Chen; Guoqi Yu; Yun-Bing Zhou

doi:10.1055/a-1499-8742

Synthesis, Table of Contents

Synthesis 2021; 53(19): 3621-3629
DOI: 10.1055/a-1499-8742

paper

Synthesis of β-Hydroxy Aryl Selenides via Transition-Metal-Free Three-Component Reaction of Arylamines, Elemental Selenium, and Epoxides

Hongwei Wang‡

^aCollege of Medicine, Shaoxing University, Shaoxing 312000, P. R. of China

^bZhejiang Engineering Research Center of Fat-Soluble Vitamin, Shaoxing 312000, P. R. of China

,

Hongchen Li‡

^cCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China

,

Yalong Bai

^bZhejiang Engineering Research Center of Fat-Soluble Vitamin, Shaoxing 312000, P. R. of China

^dZhejiang Medicine CO, Ltd., Changhai Company, Shaoxing 312000, P. R. of China

,

Yanling Hei

^bZhejiang Engineering Research Center of Fat-Soluble Vitamin, Shaoxing 312000, P. R. of China

^dZhejiang Medicine CO, Ltd., Changhai Company, Shaoxing 312000, P. R. of China

,

Junwei Chen

^bZhejiang Engineering Research Center of Fat-Soluble Vitamin, Shaoxing 312000, P. R. of China

^dZhejiang Medicine CO, Ltd., Changhai Company, Shaoxing 312000, P. R. of China

,

Guoqi Yu ∗

^aCollege of Medicine, Shaoxing University, Shaoxing 312000, P. R. of China

^bZhejiang Engineering Research Center of Fat-Soluble Vitamin, Shaoxing 312000, P. R. of China

,

Yun-Bing Zhou∗

^cCollege of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China

› Author Affiliations

Abstract

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Abstract

An efficient protocol for the construction of valuable β-hydroxy aryl selenides from easily available arylamines, elemental selenium, and epoxides through a transition-metal-free radical process is described. A wide variety of β-hydroxy aryl selenides were obtained in good to excellent yields with excellent stereo- and regioselectivity. In this reaction, two C–Se bonds can be built along with the cleavage of a C–N and C–O bond, demonstrating the high step economy and efficiency of this approach.

Key words

arylamines - elemental selenium - β-hydroxy aryl selenides - epoxides - radical reactions

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References

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