Copper-Catalyzed Intramolecular Annulation of Conjugated Enynones to Substituted 1H-Indenes and Mechanistic Studies

doi:10.1021/acs.joc.8b02064

	Copper-Catalyzed Intramolecular Annulation of Conjugated Enynones to Substituted 1H-Indenes and Mechanistic Studies
	Pei, Chao 2; Rong, Guang-Wei 2; Yu, Zhi-Xiang 3; Xu, Xin-Fang 1,2
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2018-11-02
卷号	83 期号:21 页码:13243-13255
ISSN号	0022-3263
DOI	10.1021/acs.joc.8b02064
通讯作者	Yu, Zhi-Xiang(yuzx@pku.edu.cn) ; Xu, Xin-Fang(xinfangxu@suda.edu.cn)
英文摘要	Herein, 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.
资助项目	National 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]
WOS关键词	ENE-YNE-KETONES ; CARBENE MIGRATORY INSERTION ; (2-FURYL)CARBENE COMPLEXES ; DIAZO-COMPOUNDS ; CYCLOPROPANATION REACTIONS ; REGIOSELECTIVE SYNTHESIS ; TERMINAL ALKYNES ; CROSS-COUPLINGS ; METAL CARBENE ; FURANS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000449443200028
资助机构	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 ; 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
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/166692]
专题	大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者	Yu, Zhi-Xiang; Xu, Xin-Fang
作者单位	1.Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510006, Guangdong, Peoples R China 2.Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China 3.Peking Univ, Beijing Natl Lab Mol Sci BNLMS, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China
推荐引用方式 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.