Citation: Wang Yan, Zhou Hao, Xu Ke, Shen Mei-Hua, Xu Hua-Dong. Rhodium catalyzed regioselective arene homologation of aryl urea via double C-H bond activation and migratory insertion of alkyne[J]. Chinese Chemical Letters, ;2017, 28(1): 92-96. doi: 10.1016/j.cclet.2016.05.011 shu

Rhodium catalyzed regioselective arene homologation of aryl urea via double C-H bond activation and migratory insertion of alkyne

School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou 213164, China

Corresponding author: Shen Mei-Hua, shenmh@cczu.edu.cn Xu Hua-Dong, hdxu@cczu.edu.cn
Received Date: 21 March 2016
Revised Date: 19 April 2016
Accepted Date: 9 May 2016
Available Online: 24 January 2016

Figures(3)

A convenient rhodium catalyzed oxidative arene homologation of aniline derivatives with symmetrical or unsymmetrical alkynes using Cu (OAc)₂ as oxidant is described. Urea group is shown to be effective as a directing group for initial ortho C-H activation. Two migratory insertion events of alkyne into Rh-C bond occur successively, both with complete regioselectivity. This method is particularly useful for synthesis of polyarenes with different substituents, which has not been reported with conventional protocol. A mechanism has been proposed to explain the observed data.
- Urea,
- Directing group,
- C-H Activation,
- Arene homologation,
- Asymmetric alkynes,
- Oxidative cyclization
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