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 Csp(3)-H bond cleavage with CO and various nucleophiles [(PrOH)-Pr-i, CF3CH2OH, H(CF2)(2)CH2OH, HC equivalent to CCH2OH, morpholine, diethylamine, furan, thiophene, and anisole] in the presence of the superelectrophilic complex, CBr4 center dot 2A1Br(3) 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. (c) 2013 Elsevier Ltd. All rights reserved.