A general protocol for -difluoromethylation of aniline derivatives is developed. Commercially available ethyl bromodifluoroacetate serves as a difluorocarbene source in the presence of a base. This carbene surrogate is attractive owing to its favorable stability, environmental friendliness and inexpensiveness. This reaction system features notable operational simplicity (bench top-grade solvents can be used without any pre-drying and do not require inert atmosphere protection). A wide range of functional groups in aniline derivatives are well-tolerated, and good-to-excellent product yields are generally obtained.
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http://dx.doi.org/10.1039/d2ob00119e | DOI Listing |
J Org Chem
March 2024
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
A practical and efficient copper-catalyzed carbocyclization of 2-functionalized anilines with ethyl bromodifluoroacetate has been developed. Ethyl bromodifluoroacetate is employed as the C1 source via quadruple cleavage in this transformation. This reaction can afford a variety of -containing heterocyclics with satisfactory yields and excellent functional group compatibility.
View Article and Find Full Text PDFOrg Lett
April 2023
Institute of Next Generation Matter Transformation, College of Material Sciences Engineering at Huaqiao University, 668 Jimei Blvd, Xiamen, Fujian 361021, P. R. China.
A convenient method for the synthesis of fluorine-containing heterocyclic compounds was developed by a copper-catalyzed free radical addition reaction of alkynol and ethyl bromodifluoroacetate. This strategy involves copper-catalyzed free radical addition and molecular lactone exchange of ethynyl alcohol and ethyl bromodifluoroacetate. The method is characterized by easy availability of raw materials, good stereochemical selectivity, and simple operation.
View Article and Find Full Text PDFRSC Adv
February 2023
Jiangsu Provincial Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin Normal University Huai'an 223300 Jiangsu China
A simple and effective method for the copper-catalyzed selective C5-H bromination and difluoromethylation of 8-aminoquinoline amides with ethyl bromodifluoroacetate as the bifunctional reagent was developed. The combination of cupric catalyst and alkaline additive results in a C5-bromination reaction, whereas cuprous catalyst combined with silver additive results in the C5-difluoromethylation reaction. This method has a broad substrate scope and allows for easy and convenient access to desired C5-functionalized quinolones with good to excellent yields.
View Article and Find Full Text PDFChem Sci
August 2022
Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences 116023 Dalian Liaoning China
The introduction of fluorine atoms into organic molecules is an attractive but challenging topic. In this work, an interesting palladium-catalyzed difluoroalkylative carbonylation of aryl olefins has been developed. A wide range of aryl olefins were transformed into the corresponding difluoropentanedioate compounds with good functional-group tolerance and excellent regioselectivity.
View Article and Find Full Text PDFOrg Biomol Chem
March 2022
Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong, P.R. China.
A general protocol for -difluoromethylation of aniline derivatives is developed. Commercially available ethyl bromodifluoroacetate serves as a difluorocarbene source in the presence of a base. This carbene surrogate is attractive owing to its favorable stability, environmental friendliness and inexpensiveness.
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