Synthesis of β-Arylseleno Sulfoximines: A Metal-Free Three-Component Reaction Mediated by Tetrabutylammonium Tribromide

Abstract

A tetrabutylammonium tribromide-mediated three-component reaction of alkenes, diselenides, and sulfoximines has been established herein, providing direct and metal-free access to diverse β-arylseleno sulfoximine derivatives. This regioselective sulfoximido-selenization protocol proceeds efficiently under mild and ambient conditions with generally good yields. This strategy is featured by step and atom economy, practicability, a broad substrate scope, and gram-scale synthesis.

Recent Developments in Selenylation and Thiolation of Alkenes via Three‐component Reactions

“…Moreover, this condition was also useful for the ArSBr‐mediated oxychalcogenation to construct C−S bonds. Liu and co‐workers [15b] described three‐component aminoselenation 8.3 from NH‐sulfoximines. The reaction condition was mild.…”

Three-Component Oxychalcogenation of Alkenes under Metal-Free Conditions: A Tetrabutylammonium Tribromide-Catalyzed System

“…Thus, it was questioned whether TBATB could facilitate the generation of chalcogenium ions RE + and induce the following difunctionalization reactions. The validation and implementation of this hypothesis are provided herein, as part of our ongoing effort to build and utilize chalcogen-containing compounds …”

Versatile electrooxidative amino- and oxyselenation of alkenes

“…The direct selenofunctionalisation of alkene skeletons with the formation of adjacent C-Se and C-X (X = carbon and heteroatoms) bonds has been proved to be a straightforward and powerful protocols for synthesising organic selenium-containing products. [18][19][20][21][22][23][24][25][26][27][28][29][30] However, the use of transition-metal catalysts, excessive chemical oxidants, various reaction additives, and harsh reaction conditions of some of the methods mentioned above usually result in unwanted byproducts and large amounts of waste, thus increasing the difficulties of the workup procedure and bringing the risk of environmental pollution.…”