Abstract
N-Heterocyclic carbene (NHC) derived 3-azabutadienes 1 and 2 have been prepared by a single-step reaction of the corresponding NHC with cyclohexyl isocyanide. Compound 1 features π-basic, delocalized nucleophilic sites over the 3-azabutadiene moiety, therefore allowing for coordinating with small Lewis acids, such as AlCl3 , GaCl3 , and Me2 SAuCl, to form diverse classic Lewis adducts 3-5. Combination of 1 with B(C6 F5 )3 or [Ph3 C][B(C6 F5 )4 ] resulted in single-electron transfer and the obtained radical cation was detected by EPR. In addition, a frustrated Lewis pair comprised of the π-basic 1 and BPh3 effects the splitting of the O-H bond of phenol and the N-H bond of imidazole to give 7 and 8, respectively. An intrinsic bond orbital (IBO) analysis of the pathway leading to 8 showcases the transformation of the delocalized π-electrons of 1 to a newly formed C-H localized σ-bond.
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