Electrophilic Selenium Catalysis with Electrophilic N-F Reagents as the Oxidants

Ruizhi Guo; Lihao Liao; Xiaodan Zhao

doi:10.3390/molecules22050835

Electrophilic Selenium Catalysis with Electrophilic N-F Reagents as the Oxidants

Molecules. 2017 May 19;22(5):835. doi: 10.3390/molecules22050835.

Authors

Ruizhi Guo¹, Lihao Liao², Xiaodan Zhao³

Affiliations

¹ Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China. grz616263@163.com.
² Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China. liaolih@mail2.sysu.edu.cn.
³ Institute of Organic Chemistry & MOE Key Laboratory of Bioinorganic and Synthetic Chemistry, School of Chemistry, Sun Yat-Sen University, Guangzhou 510275, China. zhaoxd3@mail.sysu.edu.cn.

Abstract

A suitable oxidative system is crucial to electrophilic selenium catalysis (ESC). This short review offers the overview of recent development in ESC with electrophilic N-F reagents as the oxidants. Several highly selective transformations of alkenes such as allylic or vinylic imidation, pyridination, syn-dichlorination, oxidative cyclization and asymmetric cyclization have been described.

Keywords: alkenes; electrophilic fluorinating reagents; regioselectivity; selenium catalysis; stereoselectivity.

Publication types

Review

MeSH terms

Alkenes / chemistry*
Benzofurans / chemical synthesis
Catalysis
Cyclization
Imidoesters / chemistry*
Indoles / chemical synthesis
Molecular Structure
Organoselenium Compounds / chemistry*
Oxidants / chemistry*
Oxidation-Reduction
Pyridines / chemistry
Stereoisomerism
Sulfonamides / chemistry*

Substances

Alkenes
Benzofurans
Imidoesters
Indoles
Organoselenium Compounds
Oxidants
Pyridines
Sulfonamides
N-fluorobenzenesulfonimide