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

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.

Selenium-π-Acid Catalyzed Oxidative Functionalization of Alkynes: Facile Access to Ynones and Multisubstituted Oxazoles

“…Organoselenium catalysis has emerged as a powerful tool for the synthesis of various compounds. − As an important part in this field, selenium-π-acid catalysis through electrophilic interactions between selenenium and π bond is different with peroxyseleninic acid catalysis probably through oxygen transfer to π bond. ,, This catalysis has garnered considerable attention in recent years because selenium-π-acid exhibits a distinct carbophilicity to alkene π bond . As a result, catalytic oxidative functionalization of alkenes has been well established. , Generally, this transformation goes through nucleophilic ring opening of seleniranium intermediate and then oxidation of alkyl selenium species followed by syn -H elimination or S N 2 displacement (Scheme a, top).…”

Combination of Lewis Basic Selenium Catalysis and Redox Selenium Chemistry: Synthesis of Trifluoromethylthiolated Tertiary Alcohols with Alkenes

“…Organoselenium catalysis has received considerable attention from chemists because of its merits in organic synthesis: mild reaction conditions, good functional group tolerance, and excellent selectivities . Furthermore, some transformations which are difficult to achieve by other methods could be accomplished by selenium catalysis .…”

Methylselenized Glucose: Improvement of the Stability of Glucose-Supported Selenium via the End-Capping Strategy

“…Selenium (Se) is a necessary trace element for animals with unique bio- and chemical activities. − Investigations on the science of selenium involve multidisciplines and have recently attracted extensive interest because Se-containing compounds and materials are widely employed as building blocks in organic synthesis, − as catalysts in fine chemical production, − as bioactive components in pharmaceutical development, , as functional constituents in materials science, − and as fertilizers, feed additives, or pesticides in agricultural and food chemistry . In the field, glucose-supported selenium is a novel material with comprehensive applications.…”