| Rhodium catalyzed regioselective arene homologation of aryl urea via double C–H bond activation and migratory insertion of alkyne |
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| 引用本文： | Yan Wang,Hao Zhou,Ke Xu,Mei-Hua Shen,Hua-Dong Xu. Rhodium catalyzed regioselective arene homologation of aryl urea via double C–H bond activation and migratory insertion of alkyne[J]. 中国化学快报, 2017, 28(1): 92-96. DOI: 10.1016/j.cclet.2016.05.011 |
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| 作者姓名： | Yan Wang Hao Zhou Ke Xu Mei-Hua Shen Hua-Dong Xu |
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| 作者单位： | School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou 213164, China |
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| 基金项目： | We are grateful for the National Natural Science Foundation of China (No. 21272077), the Natural Science Foundation of Jiangsu Province (No. BK20131143), Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) for financial support. |
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| 摘 要： | 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.
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Rhodium catalyzed regioselective arene homologation of aryl urea via double C-H bond activation and migratory insertion of alkyne |
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| Yan Wang,Hao Zhou,Ke Xu,Mei-Hua Shen,Hua-Dong Xu. 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 |
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| Authors: | Yan Wang Hao Zhou Ke Xu Mei-Hua Shen Hua-Dong Xu |
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| Affiliation: | School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou 213164, China |
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| Abstract: | 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. |
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| Keywords: | Urea Directing group C-H Activation Arene homologation Asymmetric alkynes Oxidative cyclization |
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