Transmetalation

The transmetalation is a chemical reaction in which organic radicals organometallic compounds of a metal of a second to be transmitted. In the narrower sense, the term is used primarily for the reaction of organometallic compounds with elemental metals, and in a broader sense also for the exchange of the organic residues of two organometallic compounds. Transmetallations usually take place from the more noble to the less noble metal.

Reactions

The transmetalation of an organometallic compound of the metal M ¹ with an elemental metal (M) yields the metal organyl MR.

${\displaystyle \mathrm {M+M^{1}R\longrightarrow MR+M^{1}} }$

In the reaction in the sense of a metal exchange reaction, the organic residues bound to the metals are exchanged with one another:

${\displaystyle \mathrm {[M]{-}R+[M^{1}]{-}R^{1}\longrightarrow [M]{-}R^{1}+[M^{1}]{-}R} }$

The reaction of a metal organyl with a metal salt or a complex that carries a leaving group proceeds in the sense of a metathesis reaction :

${\displaystyle \mathrm {[M]{-}X+[M^{1}]{-}R\longrightarrow [M]{-}R+[M^{1}]{-}X} }$

This reaction is important in many transition-metal-catalyzed cross-couplings, for example the Sonogashira coupling .

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• Jan Bülle, Aloys Hüttermann: The basic knowledge of organic chemistry . 1st edition Wiley-VCH, Weinheim 2000, ISBN 978-3-527-30847-7 , later as: Stefan Bräse u. a .: Organic and bio-organic chemistry. The basic knowledge for master's and diploma exams . Wiley-VCH, Weinheim 2008, ISBN 978-3-527-32012-7 .