Visible-light-initiated tandem synthesis of difluoromethylated oxindoles in 2-MeTHF under additive-, metal catalyst-, external photosensitizer-free and mild conditions

An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles through a visible-light-induced one-pot tandem reaction of N-arylacrylamides, difluoroacetic acid and PhI(OAc)2 was developed. This reaction proceeded in the absence of any additive, base, metal-catalyst and externa...

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Published in	Chinese chemical letters Vol. 32; no. 6; pp. 1907 - 1910
Main Authors	Gui, Qing-Wen, Teng, Fan, Li, Zhou-Chao, Xiong, Zhi-Yuan, Jin, Xue-Feng, Lin, Ying-Wu, Cao, Zhong, He, Wei-Min
Format	Journal Article
Language	English
Published	NEW YORK Elsevier B.V 01.06.2021 Elsevier College of Chemistry and Materials Science,Hunan Agricultural University,Changsha 410128,China%School of Chemistry and Chemical Engineering,University of South China,Hengyang 421001,China%Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation,Changsha University of Science and Technology,Changsha 410114,China
Subjects	2-MeTHF Chemistry Chemistry, Multidisciplinary External photosensitizer-free Green chemistry Physical Sciences Science & Technology Tandem reaction Visible light Visible light 2-MeTHF Green chemistry External photosensitizer-free Tandem reaction REAGENTS RADICAL CASCADE REACTION N-ARYLACRYLAMIDES FLUORINATED 3,3-DISUBSTITUTED 2-OXINDOLES PHOTOCATALYST ACTIVATED ALKENES QUINOXALIN-2(1H)-ONES CYCLIZATION
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Abstract	An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles through a visible-light-induced one-pot tandem reaction of N-arylacrylamides, difluoroacetic acid and PhI(OAc)2 was developed. This reaction proceeded in the absence of any additive, base, metal-catalyst and external photosensitizer, using cheap CHF2CO2H as a difluoromethylation reagent and bulk biomass-derived 2-MeTHF as a solvent. [Display omitted] An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles through a visible-light induced one-pot tandem reaction of N-arylacrylamides, difluoroacetic acid and PhI(OAc)2 was developed. This reaction proceeded in the absence of any additive, base, metal-catalyst and external photosensitizer, using cheap and easily available CHF2CO2H as the difluoromethylation reagent and bulk biomass-derived 2-MeTHF as the sole solvent. 26 Examples of N-arylacrylamide substrates were investigated, and all of them successfully underwent difluoromethylation to deliver the target products in good to excellent yields.
AbstractList	An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles through a visible-light induced one-pot tandem reaction of N-arylacrylamides, difluoroacetic acid and PhI(OAc)2 was developed. This reaction proceeded in the absence of any additive, base, metal-catalyst and external photosensitizer, using cheap and easily available CHF2CO2H as the difluoromethylation reagent and bulk biomass-derived 2-MeTHF as the sole solvent. 26 Examples of N-arylacrylamide substrates were investigated, and all of them successfully underwent difluoromethylation to deliver the target products in good to excellent yields. An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles through a visible-light induced one-pot tandem reaction of N-arylacrylamides, difluoroacetic acid and Phl(OAc)(2) was developed. This reaction proceeded in the absence of any additive, base, metal-catalyst and external photosensitizer, using cheap and easily available CHF2CO2H as the difluoromethylation reagent and bulk biomass-derived 2-MeTHF as the sole solvent. 26 Examples of N-arylacrylamide substrates were investigated, and all of them successfully underwent difluoromethylation to deliver the target products in good to excellent yields. (C) 2021 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved. An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles through a visible-light-induced one-pot tandem reaction of N-arylacrylamides, difluoroacetic acid and PhI(OAc)2 was developed. This reaction proceeded in the absence of any additive, base, metal-catalyst and external photosensitizer, using cheap CHF2CO2H as a difluoromethylation reagent and bulk biomass-derived 2-MeTHF as a solvent. [Display omitted] An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles through a visible-light induced one-pot tandem reaction of N-arylacrylamides, difluoroacetic acid and PhI(OAc)2 was developed. This reaction proceeded in the absence of any additive, base, metal-catalyst and external photosensitizer, using cheap and easily available CHF2CO2H as the difluoromethylation reagent and bulk biomass-derived 2-MeTHF as the sole solvent. 26 Examples of N-arylacrylamide substrates were investigated, and all of them successfully underwent difluoromethylation to deliver the target products in good to excellent yields.
Author	Teng, Fan Jin, Xue-Feng Gui, Qing-Wen Li, Zhou-Chao He, Wei-Min Xiong, Zhi-Yuan Lin, Ying-Wu Cao, Zhong
AuthorAffiliation	College of Chemistry and Materials Science,Hunan Agricultural University,Changsha 410128,China%School of Chemistry and Chemical Engineering,University of South China,Hengyang 421001,China%Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation,Changsha University of Science and Technology,Changsha 410114,China
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Keywords	Visible light 2-MeTHF Green chemistry External photosensitizer-free Tandem reaction REAGENTS RADICAL CASCADE REACTION N-ARYLACRYLAMIDES FLUORINATED 3,3-DISUBSTITUTED 2-OXINDOLES PHOTOCATALYST ACTIVATED ALKENES QUINOXALIN-2(1H)-ONES CYCLIZATION
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publication-title: GREEN CHEMISTRY doi: 10.1039/d0gc02149k
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Snippet	An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles through a visible-light-induced one-pot tandem reaction of... An efficient and eco-friendly protocol for synthesizing difluoromethylated oxindoles through a visible-light induced one-pot tandem reaction of...
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SubjectTerms	2-MeTHF Chemistry Chemistry, Multidisciplinary External photosensitizer-free Green chemistry Physical Sciences Science & Technology Tandem reaction Visible light
Title	Visible-light-initiated tandem synthesis of difluoromethylated oxindoles in 2-MeTHF under additive-, metal catalyst-, external photosensitizer-free and mild conditions
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