Transmetalation: a fundamental organometallic reaction critical to synthesis and catalysis

Abstract

A number of critical reactions form the foundation of organometallic chemistry. One such fundamental reaction of organometallic chemistry is transmetalation, a general term that in its modern meaning describes the transfer of carbon ligands (i.e., alkyl, aryl, alkynyl, allyl, etc.) from one metal to another. Transmetalation has a very long history and the reaction dates back to the early beginnings of organometallic chemistry with the work of the English chemist Edward Frankland (1825–1899) in the 1860s. Since its introduction, transmetalation has found significant utility in synthetic chemistry, allowing the generation of a wide variety of organometallic compounds of both main group and transition metal elements, and has been identified as a critical step in many synthetic organic reactions catalyzed by transition metal complexes. Regardless of the long history of this reaction and its significant applications, transmetalation is not covered in the same depth as other fundamental reactions in organometallic chemistry and is rarely given serious treatment in organometallic textbooks. Thus, the aim of the current work is to supplement current textbooks by presenting the basics of what is currently known about the details and parameters of this important reaction.