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Synthesis of CHF2-containing heterocycles through oxy-difluoromethylation using low-cost 3D printed PhotoFlow reactors

Synthesis of CHF2-containing heterocycles through oxy-difluoromethylation using low-cost 3D printed PhotoFlow reactors

Zhang, Jinlei, Selmi-Higashi, Elias, Zhang, Shen, Jean, Alexandre, Hilton, Stephen T., Couso Cambeiro, Xacobe ORCID: 0000-0002-7365-7201 and Arseniyadis, Stellios (2024) Synthesis of CHF2-containing heterocycles through oxy-difluoromethylation using low-cost 3D printed PhotoFlow reactors. Organic Letters. ISSN 1523-7060 (Print), 1523-7052 (Online) (doi:https://doi.org/10.1021/acs.orglett.3c03997)

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Abstract

We report here a highly straightforward access to a variety of CHF2-containing heterocycles, including lactones, tetrahydrofurans, tetrahydropyrans, benzolactones, phthalanes, and pyrrolidines, through a visible light-mediated intramolecular oxy-difluoromethylation under continuous flow. The method, which relies on the use of readily available starting materials, low-cost 3D printed photoflow reactors, and difluoromethyltriphe-nylphosphonium bromide used here as a CHF2 radical precursor, is practical and scalable and provides the desired products in moderate to excellent yields and excellent regio- and stereoselectivities

Item Type: Article
Additional Information: This article is part of the Organic Chemistry Driven by Academic-Industrial Collaborations special issue.
Uncontrolled Keywords: oxydifluoromethylation; difluoromethyl; alkene; photoredox; flow chemistry; photocatalysis
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
T Technology > TP Chemical technology
Faculty / School / Research Centre / Research Group: Faculty of Engineering & Science
Faculty of Engineering & Science > School of Science (SCI)
Last Modified: 10 Jan 2024 11:12
URI: http://gala.gre.ac.uk/id/eprint/45285

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