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题名: Cp*Co-III-Catalyzed Branch-Selective Hydroarylation of Alkynes via C-H Activation: Efficient Access to alpha-gem-Vinylindoles
作者: Zhou, Xukai1, 2;  Luo, Yixin3;  Kong, Lingheng1, 2;  Xu, Youwei1, 2;  Zheng, Guangfan1;  Lan, Yu3;  Li, Xingwei1
关键词: C-H activation ;  cobalt ;  indole ;  hydroarylation ;  alkyne insertion
刊名: ACS CATALYSIS
发表日期: 2017-10-01
DOI: 10.1021/acscatal.7b02248
卷: 7, 期:10, 页:7296-7304
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Physical
研究领域[WOS]: Chemistry
英文摘要: An efficient, atom-economical, and regioselective insertion of indoles into terminal alkynes has been realized via cobalt(III)-catalyzed C-H activation under mild conditions, leading to efficient synthesis of alpha-gem-vinylindoles. The insertion of the alkynes follows a rare 1,2-selectivity, and silyl alkynes, alkyl alkynes, propargyl alcohols, and protected propargyl amines are all applicable. The mechanism of this hydroarylation system has been studied in detail by a combination of experimental and computational approaches. In the reaction of silyl terminal alkynes, the regioselectivity is dictated by the steric effects of the alkyne substituent, especially in the protonolysis stage. However, for protected propargyl amines, the selectivity results from electronic effects during the insertion step, with protonolysis being insignificant in the determination of selectivity. An internal alkyne also coupled in high efficiency but with low regioselectivity. Comparisons of cobalt, rhodium, and iridium catalysts have also been made in terms of regioselectivity and reactivity, and both are high for cobalt catalysts.
关键词[WOS]: AB-INITIO PSEUDOPOTENTIALS ;  REDOX-NEUTRAL SYNTHESIS ;  BOND ACTIVATION ;  TERMINAL ALKYNES ;  INTERNAL ALKYNES ;  STEREOSELECTIVE HYDROARYLATION ;  3+2 CYCLOADDITION ;  COBALT CATALYSIS ;  DIRECTING GROUPS ;  INDOLE SYNTHESIS
语种: 英语
WOS记录号: WOS:000412795700100
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/150232
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Chongqing Univ, Sch Chem & Chem Engn, Chongqing 400030, Peoples R China

Recommended Citation:
Zhou, Xukai,Luo, Yixin,Kong, Lingheng,et al. Cp*Co-III-Catalyzed Branch-Selective Hydroarylation of Alkynes via C-H Activation: Efficient Access to alpha-gem-Vinylindoles[J]. ACS CATALYSIS,2017,7(10):7296-7304.
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