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Ruthenium(II)-Catalyzed Regioselective Ortho C-H Allenylation of Electron-Rich Aniline and Phenol Derivatives

文献类型：期刊论文

作者Chen, Yanni3,4; Hu, Liuyu3,6; Liang, Liuchun5; Guo, Fujiang5; Yang, Yaxi3; Zhou, Bing1,2,3
刊名JOURNAL OF ORGANIC CHEMISTRY
出版日期2020-02-21
卷号85期号:4页码:2048-2058
ISSN号0022-3263
DOI10.1021/acs.joc.9b02787
通讯作者Zhou, Bing(zhoubing@simm.ac.cn)
英文摘要Ortho C-H allenylation of electron-rich benzene derivatives with propargylic alcohol derivatives has been a challenge, due to their great innate tendency toward a para C-H allenylation via an SN2'-type substitution process. Here, we described a Ru(II)-catalyzed regioselective ortho C-H allenylation of electron-rich aniline and phenol derivatives, which allows the previously challenging synthesis of a broad range of ortho allenylated aniline and phenol derivatives. More significantly, highly optically active fully substituted allenes can also be prepared with high enantiomeric excess via a highly efficient chirality transfer. No para C-H allenylation product was observed in the current catalytic system, thus showing a complete reversibility of the regioselectivity.
WOS关键词SIMPLE INDOLE ALKALOIDS ; BOND FUNCTIONALIZATIONS ; ASYMMETRIC-SYNTHESIS ; EFFICIENT SYNTHESIS ; NATURAL-PRODUCTS ; ARYL HALIDES ; ACTIVATION ; ALKYLATION ; ARYLATIONS
资助项目National Natural Science Foundation of China[21702218] ; National Natural Science Foundation of China[81973166] ; National Natural Science Foundation of China[91753207] ; National Science and Technology Major Project major new drug creation[2018ZX09711002-006] ; National Science and Technology Major Project major new drug creation[2018ZX09711002-007] ; 1000-Youth Talents Plan ; Youth Innovation Promotion Association[2017333] ; K. C. Wong Education Foundation ; Science and Technology Commission of Shanghai Municipality[18431907100] ; Shanghai Rising-Star Program[17QA1405000]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000516665800025
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/280950]  
专题新药研究国家重点实验室
通讯作者Zhou, Bing
作者单位1.Univ Chinese Acad Sci, 19 Yuquan Rd, Beijing 100049, Peoples R China
2.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Hangzhou 310024, Zhejiang, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China
4.Nanchang Univ, Coll Pharm, Nanchang 330006, Jiangxi, Peoples R China
5.Shanghai Univ Tradit Chinese Med, 1200 Cailun Rd, Shanghai 201203, Peoples R China
6.Nanjing Univ Chinese Med, Coll Pharm, Nanjing 210013, Jiangsu, Peoples R China
推荐引用方式
GB/T 7714		 Chen, Yanni,Hu, Liuyu,Liang, Liuchun,et al. Ruthenium(II)-Catalyzed Regioselective Ortho C-H Allenylation of Electron-Rich Aniline and Phenol Derivatives[J]. JOURNAL OF ORGANIC CHEMISTRY,2020,85(4):2048-2058.
APA Chen, Yanni,Hu, Liuyu,Liang, Liuchun,Guo, Fujiang,Yang, Yaxi,&Zhou, Bing.(2020).Ruthenium(II)-Catalyzed Regioselective Ortho C-H Allenylation of Electron-Rich Aniline and Phenol Derivatives.JOURNAL OF ORGANIC CHEMISTRY,85(4),2048-2058.
MLA Chen, Yanni,et al."Ruthenium(II)-Catalyzed Regioselective Ortho C-H Allenylation of Electron-Rich Aniline and Phenol Derivatives".JOURNAL OF ORGANIC CHEMISTRY 85.4(2020):2048-2058.

入库方式： OAI收割

来源：上海药物研究所

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