It is significant to develop novel difluoromethylation methods because of the important roles of difluoromethyl groups in the medicinal chemistry and material industries. Here, we developed a novel difluoromethylation-carboxylation and difluoromethylation-deuteration method triggered by a difluoromethyl radical generated by electroreduction of stable and easily available difluoromethyltriphenylphosphonium bromide. Various molecules containing difluoromethyl and carboxyl or deuterium groups can be synthesized through this method. The establishment of this method will provide an alternative to radical difluoromethylation reactions.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.3c02001 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Photoredox-catalysed radical difluoromethylation/cyclization of -acryloyl-2-arylbenzimidazole to access CFH-substituted benzimidazo[2,1-]isoquinolin-6(5)-ones.
Org Biomol Chem
November 2024
School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China.
An efficient visible-light-promoted cascade difluoromethylation/cyclization reaction to access various CFH-substituted benzimidazo[2,1-]isoquinolin-6(5)-ones was developed using difluoromethyltriphenylphosphonium bromide salt as the precursor of the -CFH group under mild conditions. This protocol utilized an easily accessible and inexpensive organophotocatalyst, offering the benefits of a broad substrate scope, good functional group tolerance, and good to excellent yields, in addition to a simple operational procedure. Furthermore, the reaction mechanism was subjected to investigation, and it was demonstrated that a radical pathway constitutes a single electron transfer (SET) procedure.
View Article and Find Full Text PDFAn efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible and bench-stable difluoromethyltriphenylphosphonium bromide as the precursor of the -CFH group has been developed to afford CFH-substituted polycyclic imidazoles in moderate to good yields. This strategy, along with the construction of Csp-CFH/C-C bonds, is distinguished by mild conditions, no requirement of additives, simple operation, and wide substrate scope. In addition, the mechanistic experiments have indicated that the difluoromethyl radical pathway is essential for the methodology.
View Article and Find Full Text PDFSynthesis of CHF-Containing Heterocycles through Oxy-difluoromethylation Using Low-Cost 3D Printed PhotoFlow Reactors.
Org Lett
April 2024
Department of Chemistry, Queen Mary University of London, Mile End Road, London E1 4NS, United Kingdom.
We report here a highly straightforward access to a variety of CHF-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 CHF radical precursor, is practical and scalable and provides the desired products in moderate to excellent yields and excellent regio- and stereoselectivities.
View Article and Find Full Text PDFDifluoromethylation-Carboxylation and -Deuteration of Alkenes Triggered by Electroreduction of Difluoromethyltriphenylphosphonium Bromide.
J Org Chem
December 2023
Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, China.
It is significant to develop novel difluoromethylation methods because of the important roles of difluoromethyl groups in the medicinal chemistry and material industries. Here, we developed a novel difluoromethylation-carboxylation and difluoromethylation-deuteration method triggered by a difluoromethyl radical generated by electroreduction of stable and easily available difluoromethyltriphenylphosphonium bromide. Various molecules containing difluoromethyl and carboxyl or deuterium groups can be synthesized through this method.
View Article and Find Full Text PDFCatalytic charge transfer complex enabled difluoromethylation of enamides with difluoromethyltriphenylphosphonium bromide.
Org Biomol Chem
October 2022
School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 100049, P. R. China.
A catalytic charge transfer complex strategy that enabled difluoromethylation and ethoxycarbonylmonofluoromethylation of enamides with phosphonium bromine salts has been reported. This strategy also provides a convenient approach for the synthesis of functionalized oxindoles and 1,1-diphenylethylenes with easily available phosphonium bromine salts and a catalytic amount of iodine anion.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!