Intermolecular sp3 C–H bond functionalization of alkyl alkanoates as a new method for the one-pot synthesis of functional neo alkyl alkanoates with remote functional groups

The one-pot, regioselective, remote functionalization of amides of octanoic acid [R 2 NCOC 7 H 15 , NR 2 = NH 2 , NEt 2 , NC 4 H 8 O, (morpholinyl)] via Csp 3 –H bond cleavage with CO and various nucleophiles (EtOH, i PrOH, CF 3 CH 2 OH, H(CF 2 ) 2 CH 2 OH, C 8 H 17 SH, Et 2 NH, morpholine, furan, thiophene, and anisole) in the presence of the superelectrophilic complex, CBr 4 ·2AlBr 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 4 ·2AlBr 3 has been demonstrated.