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
a   College of Medicine, Shaoxing University, Shaoxing 312000, P. R. of China
b   Zhejiang Engineering Research Center of Fat-Soluble Vitamin, ­Shaoxing 312000, P. R. of China
,
Hongchen Li
c   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
,
Yalong Bai
b   Zhejiang Engineering Research Center of Fat-Soluble Vitamin, ­Shaoxing 312000, P. R. of China
d   Zhejiang Medicine CO, Ltd., Changhai Company, Shaoxing 312000, P. R. of China
,
Yanling Hei
b   Zhejiang Engineering Research Center of Fat-Soluble Vitamin, ­Shaoxing 312000, P. R. of China
d   Zhejiang Medicine CO, Ltd., Changhai Company, Shaoxing 312000, P. R. of China
,
Junwei Chen
b   Zhejiang Engineering Research Center of Fat-Soluble Vitamin, ­Shaoxing 312000, P. R. of China
d   Zhejiang Medicine CO, Ltd., Changhai Company, Shaoxing 312000, P. R. of China
,
Guoqi Yu
a   College of Medicine, Shaoxing University, Shaoxing 312000, P. R. of China
b   Zhejiang Engineering Research Center of Fat-Soluble Vitamin, ­Shaoxing 312000, P. R. of China
,
Yun-Bing Zhou
c   College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
› Institutsangaben


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.

Supporting Information



Publikationsverlauf

Eingereicht: 23. Februar 2021

Angenommen nach Revision: 05. Mai 2021

Accepted Manuscript online:
05. Mai 2021

Artikel online veröffentlicht:
31. Mai 2021

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