Citation: Wen Hui Zhong, Ying Na Cui, Shen Min Li, Ying Ping Jia, Jing Mei Yin. The carbonylation of phenyl bromide and its derivatives under visible light irradiation[J]. Chinese Chemical Letters, ;2012, 23(1): 29-32. doi: 10.1016/j.cclet.2011.09.024 shu

The carbonylation of phenyl bromide and its derivatives under visible light irradiation

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

Received Date: 7 June 2011

The carbonylation of phenyl bromide catalyzed by Co(OAc)₂ has been investigated with PhCOPh as a sensitizer under visible light in the presence of basic additive. With strong base CH₃ONa, PhCOOCH₃ is produced in 70% yield with 100% selectivity, the similar results are also obtained with a stronger base (CH₃)₃CONa. However, with another strong base NaOH, the yield of the ester is only 40%. On the other hand, with weak base NaOAc or (n-C₄H₉)₃N, phenyl bromide cannot be carbonylated. The results of carbonylation of the six substituted phenyl bromides suggest that the activities of o, m, p-BrC₆H₄CH₃ are similar to phenyl bromide, while the activities of o, m, p-BrC₆H₄Cl are higher with the high yields (≥ 93%) of the corresponding chloro-esters. In addition, the relative position of bromine and chlorine or methyl on phenyl ring has little effect on the activity of the carbonylation.
- Carbonylation,
- Phenyl bromide,
- o, m, p-Bromotoluene,
- o, m, p-Bromochlorobenzene,
- Visible light
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