Synthesis of Phenanthrenes through Copper-Catalyzed Cross-Coupling of N-Tosylhydrazones with Terminal Alkynes

doi:10.1021/jo501489c

	Synthesis of Phenanthrenes through Copper-Catalyzed Cross-Coupling of N-Tosylhydrazones with Terminal Alkynes
	Hossain, Mohammad Lokman 1; Ye, Fei 1; Liu, Zhenxing 1; Xia, Ying 1; Shi, Yi 1; Zhou, Lei 1; Zhang, Yan 1; Wang, Jianbo 1,2
刊名	JOURNAL OF ORGANIC CHEMISTRY
	2014-09-19
卷号	79 期号:18 页码:8689-8699
ISSN号	0022-3263
DOI	10.1021/jo501489c
文献子类	Article
英文摘要	A novel protocol for the synthesis of phenanthrenes through the copper-catalyzed reaction of aromatic tosylhydrazones with terminal alkynes is explored. The reaction proceeds via the formation of an allene intermediate and subsequent six-pi-electron cyclization-isomerization, affording phenanthrene derivatives in good yields. The transformation can be performed in two ways: (1) with N-tosylhydrazones derived from [1,1'-biphenyl]-2-carbaldehydes and terminal alkynes as the starting materials and (2) with N-tosylhydrazones derived from aromatic aldehydes and 2-alkynyl biphenyls as the starting materials. This new phenanthrene synthesis uses readily available starting materials and a cheap copper catalyst and has a wide range of functional group compatibility.
WOS关键词	ORGANIC-SYNTHESIS ; PHENANTHROQUINOLIZIDINE ALKALOIDS ; CARBENE COMPLEXES ; DERIVATIVES ; CYCLIZATION ; ANNULATION ; CYCLOISOMERIZATION ; ALLENES ; PHENANTHROINDOLIZIDINE ; PHOTOLUMINESCENCE
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000342121100023
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/167296]
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	Wang, Jianbo
作者单位	1.Peking Univ, BNLMS, Key Lab Bioorgan Chem & Mol Engn, Minist Educ,Coll Chem, Beijing 100871, Peoples R China 2.Chinese Acad Sci, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
推荐引用方式 GB/T 7714	Hossain, Mohammad Lokman,Ye, Fei,Liu, Zhenxing,et al. Synthesis of Phenanthrenes through Copper-Catalyzed Cross-Coupling of N-Tosylhydrazones with Terminal Alkynes[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(18):8689-8699.
APA	Hossain, Mohammad Lokman.,Ye, Fei.,Liu, Zhenxing.,Xia, Ying.,Shi, Yi.,...&Wang, Jianbo.(2014).Synthesis of Phenanthrenes through Copper-Catalyzed Cross-Coupling of N-Tosylhydrazones with Terminal Alkynes.JOURNAL OF ORGANIC CHEMISTRY,79(18),8689-8699.
MLA	Hossain, Mohammad Lokman,et al."Synthesis of Phenanthrenes through Copper-Catalyzed Cross-Coupling of N-Tosylhydrazones with Terminal Alkynes".JOURNAL OF ORGANIC CHEMISTRY 79.18(2014):8689-8699.