Research news, Oct. 14th, 2014

 Organometallic Intermediate-Based Organic Synthesis

Organo-di-Lithio Reagents and Beyond

Wen-Xiong Zhang and Zhenfeng Xi*

Org. Chem. Front. 2014, 1, 1132–1139 (Review)

 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 can also guide the discovery of new reactions, culminating in the advancement of novel synthetic methods. Herein we provide a perspective of 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. 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.

   In this Perspective, the above-introduced research strategy on organometallic intermediate-based organic synthesis is centered with isolation and structural characterization of reactive organometallic intermediates, which usually require more time and efforts than the discovery of the reaction itself and are considerably more challenging experimentally. The isolation and study of reactive organometallic intermediates not only leads to a better understanding of their reactivity and reaction mechanisms, but can also guide the discovery of new reactions, culminating in the advancement of novel synthetic methods.