Copper-Catalyzed Selective 1,2-Difunctionalization of N‑Heteroaromatics through Cascade C–N/CC/CO Bond Formation
journal contributionposted on 2020-09-30, 21:04 authored by Qianlin He, Feng Xie, Chuanjiang Xia, Wanyi Liang, Ziyin Guo, Zhongzhi Zhu, Yibiao Li, Xiuwen Chen
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, CC, and CO 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.
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multicomponent cascadeheteroaromaticterminal alkyneschemoselectivityapplicabilityalkyl halidessequential functionalizationCopper-Catalyzedatom efficiencysubstrate scopestrategymethodFormationderivativeDifunctionalizationlate-stage functionalizationdrug moleculesCascadeconstructionBondtwo-positiongroup tolerancedifunctionalizedHeteroaromaticquinolinefriendlinessbond