Citation: Li Jin, Chen Jingzhi, Huang Wenhao, Cheng Xu. E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes[J]. Chinese Journal of Organic Chemistry, ;2018, 38(6): 1507-1515. doi: 10.6023/cjoc201712002 shu

E-Z Isomerization of 1, 5-Bromotrichloromethylation Reaction Products and Trisubstituted Styrenes

School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023

Corresponding author: Cheng Xu, chengxu@nju.edu.cn
Received Date: 2 December 2017
Revised Date: 30 January 2018
Available Online: 6 June 2018
Fund Project: the National Natural Science Foundation of China 21572099the National Natural Science Foundation of China 21332005Project supported by the National Natural Science Foundation of China (Nos. 21572099, 21332005)

Figures(3)

1, 5-Bromotrichloromethylation of α-cyclopropylstyrenes via a radical chain pathway was achieved with Ir[dF(CF₃)ppy]₂(dtbbpy)PF₆ as a photoinitiator under visible-light irradiation to give trisubstituted styrenes with Z/E ratio of 30:70. When the reaction mixture was further irradiated, the Z/E ratio could be reversed and increased to 99:1, probably via an energy-transfer pathway involving the Ir photocatalyst. This visible-light-induced catalytic isomerization protocol could also be applied to trisubstituted styrenes to obtain products with Z/E ratios up to 99:1.
- photochemistry,
- radical,
- alkene,
- isomerization
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