Citation: Yao Yun Hu, Jing Mei Yin, Da Bin Gao, Ying Ping Jia, Guang Yun Zhou, Ying Na Cui, Shen Min Li. Photopromoted carbonylation of 1-bromo-6-chlorohexane under ambient conditions[J]. Chinese Chemical Letters, ;2008, 19(5): 529-532. doi: 10.1016/j.cclet.2008.03.020 shu

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

Liaoning Key Laboratory of Bio-organic Chemistry, Dalian University, Dalian 116622, China

Received Date: 19 December 2007

Fund Project: We appreciate the National Natural Science Foundations of China (No.20372012) and the Natural Science Foundations of Liaoning (No.20032099) for the generous financial support.

Photopromoted carbonylation of 1-bromo-6-chlorohexane with CO catalyzed by CuBr₂ and CdI₂ has been carried out underambient conditions. The results indicate that the carbonylation proceeds with the major product of chlorocsterCICH₂(CH₂)₅COOCH₃ under catalysis of CuBr₂. Furthermore, the activity of the carbonylation can be improved by additionof basic additives (NaOAc, Na₃PO₄or (n-C₄H₉)₃N). Among these additives, (n-C₄H₉)₃N is the most efficient in terms of the yield ofClCH₂(CH₂)₅COOCH₃. However, the methoxycarbonyl substituting chlorine product of BrCH₂(CH₂)₅COOCH₃ is not obtained inthe presence of CdI₂. This is quite different from the carbonylation of monochloroalkane.
- Photopromoted carbonylation,
- 1-Bromo-6-chlorohexane,
- Copper bromide,
- Tri-n-hutylamine
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