Metal-free tandem oxidative C(sp(3))-H bond functionalization of alkanes and dearomatization of N-phenyl-cinnamamides: access to alkylated 1-azaspiro[4.5]decanes.

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.