Straightforward synthesis of tri- and tetra-substituted 3-trifluoromethylfurans by heterocyclization reaction of perfluoroketene dithioacetals

Jores, Clément De Saint; Mukan, Ivan; Yegorova, Tatyana V.; Harakat, Dominique; Bouillon, Jean‐Philippe

doi:10.1016/j.tet.2016.09.009

Cited by 7 publications

(1 citation statement)

References 35 publications

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“…The second strategy, circumventing those drawbacks, relies on the use of fluorinated building blocks during the heterocyclization. A review of the synthesis of fluoro and perfluoroalkyl furans was published in 2010, and a variety of other methods have been developed since, which are in most cases limited to -CF 3 furans. − …”

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Synthesis of 3-Amino-5-fluoroalkylfurans by Intramolecular Cyclization

et al. 2021

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A synthesis to access rarely described 3-amino-5-fluoroalkylfurans has been developed by cyclization of easily accessible fluorovinamides. This method is rapid and simple and affords the desired furans as hydrochloride salts in quantitative or nearly quantitative yields. It is compatible with four different fluorinated groups (-CF3, -CF2CF3, -CHF2, and -CF2Cl) and a wide range of substituents on the amine.

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confidence: 99%

Synthesis of 3-Amino-5-fluoroalkylfurans by Intramolecular Cyclization

et al. 2021

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Ligandless Copper‐Catalyzed Carboborylation of Heteroatom‐Substituted Alkynes

Liu

Zeng

2018

Adv Synth Catal

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We have developed an efficient ligandfree copper-catalyzed regio-and stereoselective carbo-borylation of heteroatom-substituted internal alkynes using bis(pinacolato)diboron as boron source and alkyl halides as an electrophile. Both chemical yields and functional group tolerance are excellent. Our method provides an efficient synthesis of tri-and tetra-substituted alkenylboronates which could be further transformed to highly substituted alkenes via subsequent cross-coupling reactions in one pot.

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Catalyst‐Free Preparation of Perfluoroalkyl‐Phosphoryl Substituted Furans from 1‐Perfluoroalkyl 1,3‐Diketones in Two Steps

Lozovskiy

Vasilyev

2020

Adv Synth Catal

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A two‐step catalyst‐free procedure for the construction of 3‐perfluoroalkyl‐2‐(phosphoryl)methyl furans from commercially available 1‐perfluoroalkyl 1,3‐diketones is reported. Propargylic alcohols, prepared by direct alkynylation of the diketones, react with PCl3 via [2,3]‐sigmatropic rearrangement – enolate cyclization sequence, leading to multifunctional furans. The reaction mechanism is supported by DFT study. In addition, the bioactivity modifying effect of phosphoryl group on 3‐perfluoroalkyl furans is depicted.magnified image

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Straightforward synthesis of tri- and tetra-substituted 3-trifluoromethylfurans by heterocyclization reaction of perfluoroketene dithioacetals

Cited by 7 publications

References 35 publications

Synthesis of 3-Amino-5-fluoroalkylfurans by Intramolecular Cyclization

Synthesis of 3-Amino-5-fluoroalkylfurans by Intramolecular Cyclization

Ligandless Copper‐Catalyzed Carboborylation of Heteroatom‐Substituted Alkynes

Catalyst‐Free Preparation of Perfluoroalkyl‐Phosphoryl Substituted Furans from 1‐Perfluoroalkyl 1,3‐Diketones in Two Steps

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