Photopromoted carbonylation of 1-bromo-6-chlorohexane under ambient conditions

Photopromoted carbonylation of 1-bromo-6-chlorohexane with CO catalyzed by CuBr2 and CdI2 has been carried out under ambient conditions. The results indicate that the carbonylation proceeds with the major product of chloroester ClCH2(CH2)5COOCH3 under catalysis of CuBr2. Furthermore, the activity of the carbonylation can be improved by addition of basic additives (NaOAc, Na3PO4 or (n-C4H9)3N). Among these additives, (n-C4H9)3N is the most efficient in terms of the yield of ClCH2(CH2)5COOCH3. However, the methoxycarbonyl substituting chlorine product of BrCH2(CH2)5COOCH3 is not obtained in the presence of CdI2. This is quite different from the carbonylation of monochloroalkane.