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 alkyl alkanoates, [ROCOCnH2n+1 (R = Me, Et, n = 7-9)] via the Csp3-H bond cleavage with CO and various nucleophiles [iPrOH, CF3CH2OH, H(CF2)2CH2OH, HCCCH2OH, morpholine, diethylamine, furan, thiophene, and anisole] in the presence of the superelectrophilic complex, CBr4·2AlBr3 has been performed for the first time. This methodology provides access to new synthetically challenging and promising groups of derivatives of dicarboxylic acids possessing a neo-structure, such as esters and amides, and aromatic or heteroaromatic ketones containing an ester group.