Development of Organic Reactions Utilizing Three Different Types of Reactivity of Magnesium Carbenoids

Abstract

α-Chloro-substituted organomagnesiums, referred to as magnesium carbenoids, are reactive intermediates that can be generated from α-chloro-substituted sulfoxides and Grignard reagents via the sulfoxide/magnesium exchange reaction. The simultaneous existence of magnesium and chlorine atoms on the carbon atom bestows intriguing reactivity on the magnesium carbenoids. The magnesium carbenoids show three different types of reactivity, namely, nucleophilic, electrophilic, and carbene-like reactivity. The diverse reactivity of magnesium carbenoids enables a variety of organic transformations. This account summarizes our recent study on the development of reactions using magnesium carbenoids and mechanistic study on the magnesium carbenoid reactions using DFT calculations.