Transmetalation: a fundamental organometallic reaction critical to synthesis and catalysis
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Transmetalation: a fundamental organometallic reaction critical to synthesis and catalysis Seth C. Rasmussen1 Received: 8 July 2020 / Accepted: 14 October 2020 © Springer Nature Switzerland AG 2020
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. Keywords Organometallics · Metal–carbon bonds · Transition metals · Main group metals
Introduction The study of organometallic chemistry involves a number of critical reactions that form the foundation of this subdiscipline. In addition to simple substitution, such reactions include oxidative addition, reductive elimination, α- and β-elimination, oxidative coupling, as well as 1,1-, 1,2-, and 1,4-migratory insertion [1–8]. Another fundamental reaction of organometallic chemistry is transmetalation (or transmetallation), 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 [9–13]. Of course, it should be pointed out that the term transmetalation has referred to a number of different processes over time. In addition to the definition given here, transmetalation has also been used at times to refer to the transfer of a metal from one organic moiety to another [14], the exchange of * Seth C. Rasmussen [email protected] 1
Department of Chemistry and Biochemistry, North Dakota State University, NDSU Dept. 2735, P.O. Box 6050, Fargo, ND 58108‑6050, USA
one metal for another in polymetallic species [15], as well as the transfer of a main group organometallic species (i.e., trialkylstannyl, trialkylsilyl, etc.) onto a transition metal [16]. Transmetalation in the modern sense 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 (1825–1
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