Novel 4,5-bis(trifluoromethyl)-1H-pyrazoles through a concise sequential iodination-trifluoromethylation reaction

Junges, Andrizia F.; Pittaluga, Everton P.; Zanatta, Nilo; Martins, Marcos A. P.; Bonacorso, Hélio G.

doi:10.1016/j.tetlet.2019.04.031

Cited by 4 publications

(2 citation statements)

References 25 publications

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“…In 2019, Bonacorso prepared a library of bis(trifluoromethyl)-substituted pyrazoles through sequential iodination and trifluoromethylation with ClCF 2 CO 2 TMS (Scheme ). In particular, iodinated pyrazoles 459 were converted into bis(trifluoromethyl)-substituted products of type 460 and 461 in 55–87% yield. The reaction was performed in DMF under heating in the presence of HMPA as an additive and CuI as a catalyst.…”

Section: Preparation Of Fluoroalkyl-substituted Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

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Fluorinated pyrazoles play an important role in medicinal chemistry, drug discovery, agrochemistry, coordination chemistry, and organometallic chemistry. Since the early 1990s, their popularity has grown exponentially. Moreover, more than 50% of all contributions on the topic have been published in the last 5 years. In this review, analysis of novel synthetic approaches to fluorinated pyrazoles that appeared in recent years is performed. A particular emphasis is devoted to a detailed consideration of reaction mechanisms. In addition, the reasons that have led to the ever-increasing popularity of fluorinated pyrazoles in various areas of science are discussed. At the end of the review, several potentially interesting but yet mostly unknown classes of fluorinated pyrazoles are outlined.

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Section: Preparation Of Fluoroalkyl-substituted Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

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“…In this work, we considered another approach to difluorodi(het)arylmethanes, which also relied on the use of (het)aryl difluoro methyl‐substituted building blocks, namely, β‐alkoxyenones of the type 1 [X = (het)aryl, Scheme ]. It should be noted that heterocyclizations of various fluorinated β‐alkoxyenones 1 (X = H, F, Cl, CF 3 , CHF 2 ) were reported in recent publications descri‐bing synthesis of fluoroalkyl‐substituted pyrazoles, isoxazoles, and pyrimidines,, , as well as other heterocycles , . However, no examples of (het)aryl difluoromethyl ‐substituted enones of the type 1 were reported to date.…”

Section: Introductionmentioning

confidence: 99%

(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

et al. 2020

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An efficient approach to the preparation of β‐alkoxyenones bearing (het)aryl difluoromethyl substituents is described. The method included acylation of acyclic or cyclic vinyl ethers with (het)aryl difluoroacetyl chlorides. The method worked well for most substrates, except aryl‐substituted derivatives bearing electron‐donating groups in o‐ or p‐positions, and heteroaromatic compounds bearing sufficiently basic nitrogen atom. Synthetic utility of (het)aryl difluoromethyl‐substituted β‐alkoxyenones as CCC bis‐electrophiles was demonstrated by heterocyclizations with common 1,2‐ and 1,3‐bis‐nucleophiles leading to compounds with (het)aryl–CF2–(het)aryl motif, in particular (het)aryl difluoromethyl‐substituted pyrazoles, isoxazoles, and pyrimidines – promising chemotypes for drug discovery.

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Chen's Reagent: A Versatile Reagent for Trifluoromethylation, Difluoromethylenation, and Difluoroalkylation in Organic Synthesis^†

Xie

2020

Chin. J. Chem.

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SummaryMethyl fluorosulfonyldifluoroacetate (FSO2CF2CO2Me or MFSDA), often called “Chen's reagent”, is commonly used to synthesize trifluoromethylated and difluoroalkylated compounds. This important reagent was initially developed as an efficient trifluoromethylating agent by Professor Qing‐Yun Chen and co‐workers at Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences in 1989. Since then, this reagent has been widely used in academia and industry for the copper‐mediated trifluoromethylation of aryl, alkenyl, and even some alkyl halides, among others. During the last decade, this reagent was further developed as a difluorocarbene precursor as well as a radical difluoroalkylating agent under visible light promoted redox catalysis. This review aims to briefly highlight the initial discovery, historical development, and synthetic applications of Chen's reagent, and provide some guidelines for readers to use Chen's reagent in their own synthesis.

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Novel 4,5-bis(trifluoromethyl)-1H-pyrazoles through a concise sequential iodination-trifluoromethylation reaction

Cited by 4 publications

References 25 publications

Fluorinated Pyrazoles: From Synthesis to Applications

Fluorinated Pyrazoles: From Synthesis to Applications

(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

Chen's Reagent: A Versatile Reagent for Trifluoromethylation, Difluoromethylenation, and Difluoroalkylation in Organic Synthesis^†

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Novel 4,5-bis(trifluoromethyl)-1H-pyrazoles through a concise sequential iodination-trifluoromethylation reaction

Cited by 4 publications

References 25 publications

Fluorinated Pyrazoles: From Synthesis to Applications

Fluorinated Pyrazoles: From Synthesis to Applications

(Het)aryl Difluoromethyl‐Substituted β‐Alkoxyenones: Synthesis and Heterocyclizations

Chen's Reagent: A Versatile Reagent for Trifluoromethylation, Difluoromethylenation, and Difluoroalkylation in Organic Synthesis†

Contact Info

Product

Resources

About

Chen's Reagent: A Versatile Reagent for Trifluoromethylation, Difluoromethylenation, and Difluoroalkylation in Organic Synthesis^†