Synthesis of CHF2‑Containing Heterocycles through Oxy-difluoromethylation Using Low-Cost 3D Printed PhotoFlow Reactors

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,...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2024-04, Vol.26 (14), p.2877-2882
Main Authors: Zhang, Jinlei, Selmi-Higashi, Elias, Zhang, Shen, Jean, Alexandre, Hilton, Stephen T., Cambeiro, Xacobe C., Arseniyadis, Stellios
Format: Article
Language:English
Subjects:
Letter
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 difluoromethyltriphenylphosphonium 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03997