Selenocyanobenziodoxolone: a practical electrophilic selenocyanation reagent and its application for solid-state synthesis of α-carbonyl selenocyanates

Jun-An Xiao; Yu-Chun Li; Xiu-Liang Cheng; Wen-Qiang Chen; Jian-Guo Cui; Yan-Min Huang; Jun Huang; Qi Xiao; Wei Su; Hua Yang

doi:10.1039/C9QO00358D

Selenocyanobenziodoxolone: a practical electrophilic selenocyanation reagent and its application for solid-state synthesis of α-carbonyl selenocyanates†

Jun-An Xiao,

*^a Yu-Chun Li,^a Xiu-Liang Cheng,^a Wen-Qiang Chen,

^a Jian-Guo Cui,^a Yan-Min Huang,^a Jun Huang,^a Qi Xiao,

^a Wei Su*^a and Hua Yang

*^b

Author affiliations

* Corresponding authors

^a Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning, P. R. China
E-mail: jaxiao@csu.edu.cn, suwmail@163.com

^b College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China
E-mail: hyangchem@csu.edu.cn

Abstract

A new electrophilic selenocyanation reagent, selenocyano-benziodoxolone, was successfully prepared from 2-iodobenzoic acid in two steps (71% overall yield). A variety of α-selenocyanated ketones and β-ketoesters, including selenocyanate-containing steroid derivatives, have been achieved by using this newly developed selenocyano-benziodoxolone in good to excellent yields (up to 99%) simply by grinding under mild conditions.

Organic Chemistry Frontiers

Selenocyanobenziodoxolone: a practical electrophilic selenocyanation reagent and its application for solid-state synthesis of α-carbonyl selenocyanates†

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Selenocyanobenziodoxolone: a practical electrophilic selenocyanation reagent and its application for solid-state synthesis of α-carbonyl selenocyanates

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