Stable carbenes are well known to resist dimerization and thus the formation of the corresponding alkene. This is due to the high energy LUMO (empty p-orbital) being inaccessible towards population by the HOMO (lone pair) of another carbene. With the exception of the use of an acid catalyst, the coupling of two individually stable carbenes had yet to have been demonstrated. It will be shown that by utilizing strongly electrophilic carbenes, such as both cyclic (alkyl) (amino) carbenes (CAACs) and diamido carbenes (DACs), coupling with strongly nucleophilic carbenes becomes possible. These carbene-carbene cross coupling reactions produced several interesting products which were studied by X-ray diffraction and NMR analysis. Among the products, the isolation of a significantly bent allene as well as the first example of a hetero-carbene dimeric species will be discussed. 

Stable carbene cross coupling reactions

248th National Meeting (2014)

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