Intramolecular Csp(3)-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

doi:10.1039/c9sc05522c

	Intramolecular Csp(3)-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines
	Wen, Xiaojin 1; Li, Xinyao 1; Luo, Xiao 1; Wang, Weijin 1; Song, Song 1,2; Jiao, Ning 1
刊名	CHEMICAL SCIENCE
	2020-05-07
卷号	11 期号:17 页码:4482-4487
ISSN号	2041-6520
DOI	10.1039/c9sc05522c
通讯作者	Song, Song(ssong@bjmu.edu.cn) ; Jiao, Ning(jiaoning@pku.edu.cn)
英文摘要	The intramolecular Csp(3)-H and/or C-C bond amination is very important in modern organic synthesis due to its efficiency in the construction of diversified N-heterocycles. Herein, we report a novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines through selective Csp(3)-H and/or C-C bond cleavage. Two C-N single bonds or a C & xe001;N double bond are efficiently constructed in these transformations. The carbocation mechanism differs from the reported metal nitrene intermediates and therefore enables metal-free and new transformation.
资助项目	National Key Research and Development Project[2019YFC1708902] ; National Natural Science Foundation of China[21632001] ; National Natural Science Foundation of China[21602005] ; National Natural Science Foundation of China[81821004] ; Drug Innovation Major Project, Peking University[2018ZX09711-001] ; Drug Innovation Major Project, Peking University[PKU2020PKYZX004] ; Shanghai Key Laboratory of Green Chemistry and Chemical Processes[2060302]
WOS关键词	C-H AMINATION ; SCHMIDT REACTION ; RING-EXPANSION ; CHEMOSELECTIVE AMINATION ; EFFICIENT SYNTHESIS ; C(SP(3))-H BONDS ; HYDROXY AZIDES ; ORGANIC AZIDES ; NITROGEN ; FUNCTIONALIZATION
WOS研究方向	Chemistry
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000532365500021
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/280348]
专题	中国科学院上海药物研究所
通讯作者	Song, Song; Jiao, Ning
作者单位	1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Wen, Xiaojin,Li, Xinyao,Luo, Xiao,et al. Intramolecular Csp(3)-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines[J]. CHEMICAL SCIENCE,2020,11(17):4482-4487.
APA	Wen, Xiaojin,Li, Xinyao,Luo, Xiao,Wang, Weijin,Song, Song,&Jiao, Ning.(2020).Intramolecular Csp(3)-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines.CHEMICAL SCIENCE,11(17),4482-4487.
MLA	Wen, Xiaojin,et al."Intramolecular Csp(3)-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines".CHEMICAL SCIENCE 11.17(2020):4482-4487.