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Visible-Light-Induced Atom Transfer Radical Addition and Cyclization of Perfluoroalkyl Halides with 1,n-Enynes

Author:
Wang, Shuo-Wen, Yu, Jian, Zhou, Qin-Yi, Chen, Si-Yu, Xu, Zhen-Hua, Tang, Shi
Source:
ACS sustainable chemistry & engineering 2019 v.7 no.11 pp. 10154-10162
ISSN:
2168-0485
Subject:
benzene, hydrogen, moieties, perfluorocarbons, pyrrolidines
Abstract:
A mild and efficient visible-light-induced atom transfer radical addition and cyclization of 1,n-enynes (n = 6, 7) with perfluoroalkyl halides, leading to halo-perfluorinated N-heterocycles, has been developed. This protocol offers a mild, completely atom-economic, and general access to perfluorinated 2,4-dihydronquinolin-2(1H)-ones and pyrrolidines from corresponding benzene and N-tethered 1,n-enynes (n = 6, 7) via 5∼6-exo-dig cyclization, allowing for the expedient incorporation of a wide variety of perfluorinated groups, such as CF₃, i/n-C₃F₇, n-C₄F₉, n-C₆F₁₃, n-C₈F₁₇, n-C₁₀F₂₁, CF₂Br, CF₂CO₂Et, etc. In addition, the reactions using 1,7-enynes (n = 6, 7) bearing a tert-butyl-linked alkynyl moiety enable a divergent cyclization involving a hydrogen atom transfer (HAT) process, thereby leading to novel α,α-halo-perfluorinated 2,4-dihydronquinolin-2(1H)-ones.
Agid:
6458582