Cyclic (alkyl)(amino)carbenes: from Replacing Metals to Metal Replacement

Stable singlet carbenes are flourishing with a diversity of applications: from ligands in catalysis to the stabilization of otherwise unisolable chemical species. Here, I will showcase the diverse and rich chemistry of cyclic (alkyl)(amino)carbenes (CAACs), a class of stable singlet carbenes known for their high ambiphilic character.

Deviating from typical carbene-organocatalysis, which is still dominated by Lewis basic carbenes, I will demonstrate that CAACs allow for catalytic processes so far restricted to transition metals. Afterward, I will illustrate how CAACs’ ambiphilicity can be further exploited to stabilize highly reactive coinage metal clusters which enabled the absolute templating of the clusters by means of galvanic metal replacement. Going a step further, I will discuss how these molecular models allowed us to better understand the reactivity of M(111) surfaces.

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