Intermolecular sp super(3) C-H bond functionalization of alkyl amides as a new method for the one-pot synthesis of functional neo alkyl amides with remote functional groups

The one-pot, regioselective, remote functionalization of amides of octanoic acid [R sub(2)NCOC sub(7)H sub(15), NR sub(2) = NH sub(2), NEt sub(2), NC sub(4)H sub(8)O, (morpholinyl)] via Csp super(3)-H bond cleavage with CO and various nucleophiles (EtOH, super(i)PrOH, CF sub(3)CH sub(2)OH, H(CF sub(2)) sub(2)CH sub(2)OH, C sub(8)H sub(17)SH, Et sub(2)NH, morpholine, furan, thiophene, and anisole) in the presence of the superelectrophilic complex, CBr sub(4).2AlBr sub(3) has been performed for the first time. This methodology provides access to new synthetically challenging and promising derivatives of amides with remote functional groups of neo-structure. The oxidative cyclization of octanamide into a six-membered cyclic amide with the C(Me)Et group adjacent to the heteroatom using CBr sub(4).2AlBr sub(3) has been demonstrated.