Copper-Catalyzed Selective 1,2-Difunctionalization of N-Heteroaromatics through Cascade C–N/C═C/C═O Bond Formation

Autor:	He Qianlin, Feng Xie, Zhongzhi Zhu, Wanyi Liang, Xiuwen Chen, Guo Ziyin, Chuanjiang Xia, Yibiao Li
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Organic Chemistry Quinoline Halide Substrate (chemistry) Biochemistry Combinatorial chemistry chemistry.chemical_compound chemistry Atom economy Functional group Molecule Physical and Theoretical Chemistry Chemoselectivity Alkyl
Zdroj:	Organic Letters. 22:7976-7980
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.0c02910
Popis:	This study presents an efficient strategy for constructing 1,2-difunctionalized quinoline derivatives via the multicomponent cascade coupling of N-heteroaromatics with alkyl halides and different terminal alkynes. This reaction was achieved through sequential functionalization at the one- and two-positions of quinolines, which displayed a broad substrate scope, environmental friendliness, excellent functional group tolerance, high atom efficiency, and chemoselectivity. The multicomponent coupling involved the abnormal construction of new C-N, C═C, and C═O bonds in one pot. The applicability of this method was further demonstrated by the late-stage functionalization of complex drug molecules under the established conditions.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::99c777eb47c671f33e89ee3e86d5bf70 https://doi.org/10.1021/acs.orglett.0c02910 Zobrazit plný text záznamu