Metal-free tandem oxidative C(sp3)-H bond functionalization of alkanes and dearomatization of N-phenyl-cinnamamides: access to alkylated 1-azaspiro[4.5]decanesElectronic supplementary information (ESI) available. See DOI: 10.1039/c5cc07175e

The TBPB promoted tandem oxidative C(sp 3 )-H bond functionalization of simple alkanes/alkylation-initiated dearomatization of N -phenyl-cinnamamides is reported, providing a direct method for the synthesis of alkylated 1-azaspiro[4.5]decanes with excellent regioselectivity and diastereoselectivity. The formation of two C(sp 3 )-C(sp 3 ) bonds and construction of a spirodienone motif are involved in one step. Metal-free tandem C(sp 3 )-H bond functionalization of simple alkanes/dearomatization of N -phenyl-cinnamamides is developed, providing 1-azaspiro[4.5]decanes with excellent regioselectivity and diastereoselectivity.