An efficient protocol was reported for the synthesis of 2-trifluoromethyl indoles through visible-light-promoted intermolecular cyclization of sulfoxonium ylides with azides, without the need for external photocatalysts, transition metals, or bases. The formation of 2-trifluoromethyl indoles involves an intriguing cascade process including azide rearrangement, intermolecular nucleophilic addition, and visible-light-promoted cyclization of a key intermediate. The protocol features high efficiency, mild conditions, excellent substrate compatibility and good regioselectivity. The practicality of this approach is demonstrated through scale-up reactions and further modifications of the synthesized indoles.
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Visible light-induced cascade annulation of sulfoxonium ylides with azides for the synthesis of 2-trifluoromethyl indoles.
Chem Commun (Camb)
January 2025
Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China.
An efficient protocol was reported for the synthesis of 2-trifluoromethyl indoles through visible-light-promoted intermolecular cyclization of sulfoxonium ylides with azides, without the need for external photocatalysts, transition metals, or bases. The formation of 2-trifluoromethyl indoles involves an intriguing cascade process including azide rearrangement, intermolecular nucleophilic addition, and visible-light-promoted cyclization of a key intermediate. The protocol features high efficiency, mild conditions, excellent substrate compatibility and good regioselectivity.
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Bioorg Chem
December 2024
State Key Laboratory of Fine Chemicals, Department of Pharmaceutical Engineering, School of Chemical Engineering, Dalian University of Technology, 2 Linggong Road, Dalian 116024, PR China. Electronic address:
A series of 3-(2-trifluoromethyl-3-aryl-4H-chromen-4-yl)-1H-indoles (5-1 to 5-29) were developed and characterized. Most of compounds were found to be potent for inhibiting the production of NO in LPS-induced RAW264.7 cells, of which 3-(3-(4-chlorophenyl)-6-methoxy-2-(trifluoromethyl)-4H-chromen-4-yl)-1H-indole (5-25) was the most optimal (IC = 4.
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Org Lett
December 2022
Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.
An efficient two-step method for synthesizing 2-(trifluoromethyl)- and 2-(difluoromethyl)benzoheteroles bearing various substituents was developed. Commercially available HFO-1224yd() or HFO-1233yd() underwent the Suzuki-Miyaura coupling with arylboronic acids (acid esters) bearing a nucleophilic moiety at the position to yield the corresponding β-fluoro-β-(trifluoromethyl)- or β-fluoro-β-(difluoromethyl)styrenes, respectively. Treatment of the obtained styrenes with potassium phosphate induced nucleophilic 5-- cyclization to provide the corresponding 2-trifluoromethylated or 2-difluoromethylated indoles and benzofurans, as well as benzothiophenes.
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Chem Commun (Camb)
May 2022
College of Chemical Engineering, State Key Laboratory Breeding Base of Green Chemical Synthesis Technology, Zhejiang University of Technology, Chaowang Road 18#, Hangzhou, 310014, China.
Highly enantioselective palladium-catalyzed dearomative reductive Heck reaction and domino Heck-Suzuki reaction of 2-CF-indoles have been developed. Using Pd(OAc)/()-Synphos as the catalyst and EtSiH as a hydride source, a variety of indolines bearing a 2-trifluoromethyl quaternary stereocenter were obtained a dearomative reductive Heck reaction. Alternatively, using Pd(dba)/phosphoramidite as the catalyst and ArBNa as a coupling partner, structurally diverse indolines containing two vicinal carbon stereocenters were afforded through the domino dearomative Heck-Suzuki reaction.
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Eur J Med Chem
September 2019
State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing, Jiangsu, 210009, China. Electronic address:
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