Organometallic intermediate-based organic synthesis: organo-di-lithio reagents and beyond

Abstract

Metal-mediated organic reactions have become one of the great frontiers of organic synthesis. These processes usually involve multiple transient or unobservable reactive intermediates. The isolation and study of these reactive organometallic intermediates would not only lead to a better understanding of their reactivity, but also guide the discovery of new reactions, culminating in the advancement of novel synthetic methods. Herein we provide a perspective of a research strategy which focuses on organometallic intermediate-based organic synthesis. Specifically, we highlight the applications of our organo-di-lithio reagents to the synthesis of a diverse range of reactive intermediates and small molecules. A series of organo-di-lithio reagents has been synthesized, isolated, and applied in organic and organometallic synthesis. These isolated dilithio reagents can be transformed into a variety of organo-di-metallic or metallacyclic compounds via transmetallation, which in turn provides access to organic and organometallic compounds with interesting and useful properties. Selected examples by other research groups are also briefly mentioned, in which reactive organometallic intermediates are isolated for a better understanding of reaction mechanisms, and in some cases are further applied to synthesis.