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

doi:10.1021/acs.joc.9b02787

	Ruthenium(II)-Catalyzed Regioselective Ortho C-H Allenylation of Electron-Rich Aniline and Phenol Derivatives
	Chen, Yanni 1,2; Hu, Liuyu 1,5; Liang, Liuchun 3; Guo, Fujiang 3; Yang, Yaxi 1; Zhou, Bing 1,4,6
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2020-02-21
卷号	85 期号:4 页码:2048-2058
ISSN号	0022-3263
DOI	10.1021/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.
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关键词	SIMPLE INDOLE ALKALOIDS ; BOND FUNCTIONALIZATIONS ; ASYMMETRIC-SYNTHESIS ; EFFICIENT SYNTHESIS ; NATURAL-PRODUCTS ; ARYL HALIDES ; ACTIVATION ; ALKYLATION ; ARYLATIONS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000516665800025
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/280950]
专题	中国科学院上海药物研究所
通讯作者	Zhou, Bing
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China 2.Nanchang Univ, Coll Pharm, Nanchang 330006, Jiangxi, Peoples R China 3.Shanghai Univ Tradit Chinese Med, 1200 Cailun Rd, Shanghai 201203, Peoples R China 4.Univ Chinese Acad Sci, 19 Yuquan Rd, Beijing 100049, Peoples R China 5.Nanjing Univ Chinese Med, Coll Pharm, Nanjing 210013, Jiangsu, Peoples R China 6.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Hangzhou 310024, Zhejiang, 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.