The addition of BX3 (X=Cl,Br) to a 1,2-azaborole readily facilitates a 1,2-hydrogen migration resulting in a BX3- cyclic (alkyl)(amino) carbene (cAAC) adduct. Similarly, reaction of BX3 (X=Br, I) with 1,3,2-diazaborole in our laboratory prompts a 1,2-hydrogen migration to afford the BX3-abnormal N-heterocyclic carbene (aNHC) complex. This coordination of the carbene center of aNHC to BX3 is an equilibrium process. Interestingly, substituting the borole position of a 1,3,2-diazaborole could allow for a more basic aNHC than previously synthesized. The synthesis, molecular structure, and equilibrium dynamics of the aNHC and its complexes with BX3 (X=Br,I) will be discussed.

Preparation and chemistry of 1,3,2-diazaborole-derived carbene complexes of boron

256th National Meeting (2018)

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