Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

Johansen, Martin B.; Lindhardt, Anders T.

doi:10.1039/c9ob02635e

Cited by 12 publications

(10 citation statements)

References 49 publications

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“…In that project, pyrazole 452 gave CF 3 -substituted derivative 453 in 60% yield. Johansen and Lindhardt reported a [Cu]-catalyzed additivefree decarboxylative trifluoromethylation of (hetero)aromatic iodides with CF 3 CO 2 K. 183 The reaction proceeded in DMF under heating at 160 °C. Under these conditions, pyrazole 452 was converted into product 453 in 51% yield (Scheme 76).…”

Section: Other Heterocyclizationsmentioning

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: Other Heterocyclizationsmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

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“…High-resolution mass spectroscopy (HRMS) was performed using a Bruker maXis impact instrument. X-ray crystallographic measurements were performed using a Super Nova, Dual, Cu at zero, Eos diffractometer at 100 K. Compounds 5 – 8 were synthesized according to the literature procedure. , [Ni(PLY) 2 (THF) 2 ] was prepared according to the reported literature procedure …”

Section: Experimental Sectionmentioning

confidence: 99%

“…X-ray crystallographic measurements were performed using a Super Nova, Dual, Cu at zero, Eos diffractometer at 100 K. Compounds 5−8 were synthesized according to the literature procedure. 46,47 [Ni(PLY) 2 (THF) 2 ] was prepared according to the reported literature procedure. 39 Preparation of 1,3-Bis(2,6-diisopropylphenyl)-2,4-diphenylimidazolium Chloride (1).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

A Bottleable Imidazole-Based Radical as a Single Electron Transfer Reagent

et al. 2020

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Reduction of 1,3-bis(2,6-diisopropylphenyl)-2,4-diphenyl-1H-imidazol-3-ium chloride (1) resulted in the formation of the first structurally characterized imidazole-based radical 2. 2 was established as a single electron transfer reagent by treating it with an acceptor molecule tetracyanoethylene. Moreover, radical 2 was utilized as an organic electron donor in a number of organic transformations such as in activation of an aryl−halide bond, alkene hydrosilylation, and in catalytic reduction of CO 2 to methoxyborane, all under ambient temperature and pressure.Note pubs.acs.org/joc

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“… 4 Furthermore, some postcyclization, functional group interconversions leading to trifluoromethylated pyrazoles, and catalytic fluoroalkylations have been developed more recently. 5 Another powerful approach is based on 1,3-dipolar cycloadditions employing trifluoromethylated 1,3-dipoles and appropriate dipolarophiles. In the past decade, remarkable progress has been achieved in the chemistry of 2,2,2-trifluorodiazoethane; however, some drawbacks such as difficult handling, low selectivity, and the scope limited to pyrazoles lacking a substituent at N(1) have been pointed out.…”

mentioning

confidence: 99%

Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions

et al. 2022

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A general approach for preparation of two types of polyfunctionalized 3-trifluoromethylpyrazoles is reported. The protocol comprises (3 + 2)-cycloaddition of the in situ generated trifluoroacetonitrile imines with enones leading to trans -configured 5-acyl-pyrazolines in a fully regio- and diastereoselective manner. Initially formed cycloadducts were aromatized by treatment with manganese dioxide. Depending on the solvent used, the oxidation step either led to fully substituted pyrazoles (DMSO) or proceeded via a deacylative pathway to afford 1,3,4-trisubstituted derivatives (hexane) with excellent selectivity.

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Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

Abstract: Low cost and widely available Cu2O has been identified as a superior catalyst towards decarboxylative aromatic trifluoromethylations in the absence of ligands and additives.

Cited by 12 publications

References 49 publications

Fluorinated Pyrazoles: From Synthesis to Applications

Fluorinated Pyrazoles: From Synthesis to Applications

A Bottleable Imidazole-Based Radical as a Single Electron Transfer Reagent

Trifluoromethylated Pyrazoles via Sequential (3 + 2)-Cycloaddition of Fluorinated Nitrile Imines with Chalcones and Solvent-Dependent Deacylative Oxidation Reactions

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