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Cp*Co-III-Catalyzed Branch-Selective Hydroarylation of Alkynes via C-H Activation: Efficient Access to alpha-gem-Vinylindoles
Zhou, Xukai1,2; Luo, Yixin3; Kong, Lingheng1,2; Xu, Youwei1,2; Zheng, Guangfan1; Lan, Yu3; Li, Xingwei1
KeywordC-h Activation Cobalt Indole Hydroarylation Alkyne Insertion
Source PublicationACS CATALYSIS
2017-10-01
DOI10.1021/acscatal.7b02248
Volume7Issue:10Pages:7296-7304
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Physical
WOS Research AreaChemistry
WOS KeywordAB-INITIO PSEUDOPOTENTIALS ; REDOX-NEUTRAL SYNTHESIS ; BOND ACTIVATION ; TERMINAL ALKYNES ; INTERNAL ALKYNES ; STEREOSELECTIVE HYDROARYLATION ; 3+2 CYCLOADDITION ; COBALT CATALYSIS ; DIRECTING GROUPS ; INDOLE SYNTHESIS
AbstractAn 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.
Language英语
WOS IDWOS:000412795700100
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/150232
Collection中国科学院大连化学物理研究所
Affiliation1.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
GB/T 7714
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.
APA Zhou, Xukai.,Luo, Yixin.,Kong, Lingheng.,Xu, Youwei.,Zheng, Guangfan.,...&Li, Xingwei.(2017).Cp*Co-III-Catalyzed Branch-Selective Hydroarylation of Alkynes via C-H Activation: Efficient Access to alpha-gem-Vinylindoles.ACS CATALYSIS,7(10),7296-7304.
MLA Zhou, Xukai,et al."Cp*Co-III-Catalyzed Branch-Selective Hydroarylation of Alkynes via C-H Activation: Efficient Access to alpha-gem-Vinylindoles".ACS CATALYSIS 7.10(2017):7296-7304.
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