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Copper-Catalyzed Intramolecular Annulation of Conjugated Enynones to Substituted 1H-Indenes and Mechanistic Studies
Pei, Chao1; Rong, Guang-Wei1; Yu, Zhi-Xiang2; Xu, Xin-Fang1,3
Corresponding AuthorYu, Zhi-Xiang(yuzx@pku.edu.cn) ; Xu, Xin-Fang(xinfangxu@suda.edu.cn)
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
2018-11-02
ISSN0022-3263
DOI10.1021/acs.joc.8b02064
Volume83Issue:21Pages:13243-13255
Funding ProjectNational Natural Science Foundation of China[21602148] ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; project of scientific and technologic infrastructure of Suzhou[SZS201708]
Funding OrganizationNational Natural Science Foundation of China ; National Natural Science Foundation of China ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; project of scientific and technologic infrastructure of Suzhou ; project of scientific and technologic infrastructure of Suzhou ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; project of scientific and technologic infrastructure of Suzhou ; project of scientific and technologic infrastructure of Suzhou ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; project of scientific and technologic infrastructure of Suzhou ; project of scientific and technologic infrastructure of Suzhou ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; project of scientific and technologic infrastructure of Suzhou ; project of scientific and technologic infrastructure of Suzhou
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordENE-YNE-KETONES ; CARBENE MIGRATORY INSERTION ; (2-FURYL)CARBENE COMPLEXES ; DIAZO-COMPOUNDS ; CYCLOPROPANATION REACTIONS ; REGIOSELECTIVE SYNTHESIS ; TERMINAL ALKYNES ; CROSS-COUPLINGS ; METAL CARBENE ; FURANS
AbstractHerein, a copper-catalyzed intramolecular cascade reaction of conjugated enynones to deliver substituted 1H-indenes is reported. The inexpensive and less toxic copper salt served as the only catalyst in the transformation, affording the 3-(2-furyl)-substituted 1H-indenes in good to excellent yields under mild reaction conditions with broad functional group tolerance and making it highly appealing for synthetic organic chemistry. Notably, detailed DFT calculations have been carried out to elucidate that the reaction undergoes a copper-mediated 5-exo-dig cyclization of enynones to afford copper-(2-furyl)-carbene intermediate, followed by diene-carbene cyclization (one step but involving 6 pi cyclization of Cu-carbene and reductive elimination) and 1,5-hydrogen shift to provide the 1H-indenes.
Language英语
Funding OrganizationNational Natural Science Foundation of China ; National Natural Science Foundation of China ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; project of scientific and technologic infrastructure of Suzhou ; project of scientific and technologic infrastructure of Suzhou ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; project of scientific and technologic infrastructure of Suzhou ; project of scientific and technologic infrastructure of Suzhou ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; project of scientific and technologic infrastructure of Suzhou ; project of scientific and technologic infrastructure of Suzhou ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions ; project of scientific and technologic infrastructure of Suzhou ; project of scientific and technologic infrastructure of Suzhou
WOS IDWOS:000449443200028
PublisherAMER CHEMICAL SOC
Citation statistics
Cited Times:6[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/166693
Collection中国科学院大连化学物理研究所
Corresponding AuthorYu, Zhi-Xiang; Xu, Xin-Fang
Affiliation1.Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
2.Peking Univ, Beijing Natl Lab Mol Sci BNLMS, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China
3.Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China
Recommended Citation
GB/T 7714
Pei, Chao,Rong, Guang-Wei,Yu, Zhi-Xiang,et al. Copper-Catalyzed Intramolecular Annulation of Conjugated Enynones to Substituted 1H-Indenes and Mechanistic Studies[J]. JOURNAL OF ORGANIC CHEMISTRY,2018,83(21):13243-13255.
APA Pei, Chao,Rong, Guang-Wei,Yu, Zhi-Xiang,&Xu, Xin-Fang.(2018).Copper-Catalyzed Intramolecular Annulation of Conjugated Enynones to Substituted 1H-Indenes and Mechanistic Studies.JOURNAL OF ORGANIC CHEMISTRY,83(21),13243-13255.
MLA Pei, Chao,et al."Copper-Catalyzed Intramolecular Annulation of Conjugated Enynones to Substituted 1H-Indenes and Mechanistic Studies".JOURNAL OF ORGANIC CHEMISTRY 83.21(2018):13243-13255.
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