(1-Selenocyanatoethyl)benzene: A Selenocyanation Reagent for Site-Selective Selenocyanation of Inert Alkyl C(sp3)-H Bonds

Fei Yu; Chuang Li; Chuangye Wang; Hongwei Zhang; Zhong-Yan Cao

doi:10.1021/acs.orglett.1c02564

(1-Selenocyanatoethyl)benzene: A Selenocyanation Reagent for Site-Selective Selenocyanation of Inert Alkyl C(sp³)-H Bonds

Org Lett. 2021 Sep 17;23(18):7156-7160. doi: 10.1021/acs.orglett.1c02564. Epub 2021 Sep 1.

Authors

Fei Yu¹, Chuang Li¹, Chuangye Wang¹, Hongwei Zhang¹, Zhong-Yan Cao²

Affiliations

¹ Department of Chemistry, College of Science, China University of Petroleum (East China) Qingdao, Shandong 266580, China.
² College of Chemistry and Chemical Engineering, Henan University, Kaifeng, Henan 475004, China.

PMID: 34468157
DOI: 10.1021/acs.orglett.1c02564

Abstract

A new, simple, yet easily accessible, (1-selenocyanatoethyl)benzene has been designed and applied as a SeCN group transfer reagent for selenocyanation of aliphatic C(sp³)-H bonds for the first time. This protocol is featured with mild reaction conditions and wide substrate scope. Control experiments reveal that a radical-group transfer mechanism might be involved.