Acid‐Mediated Three Component Assembly of 4‐Fluoropyrazoles from α‐Fluoronitroalkenes, Hydrazines, and Aldehydes

Motornov, Vladimir; Tabolin, Andrey A.; Nelyubina, Yulia V.; Nenajdenko, Valentine G.; Ioffe, Sema L.

doi:10.1002/ejoc.202000841

Cited by 14 publications

(3 citation statements)

References 53 publications

(23 reference statements)

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“…In 2020, Tabolin and colleagues elaborated a three-component synthesis of 4-fluoropyrazoles from aldehydes, hydrazines, and α-fluoronitroalkenes (Scheme ). In that work, 23 fluoropyrazoles were synthesized in 25–81% yield. Both electron-rich and electron-deficient nitroalkenes as well as different hydrazones derived from aromatic aldehydes were used.…”

Section: Preparation Of Fluoro-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 Fluoro-substituted Pyrazolesmentioning

confidence: 99%

Fluorinated Pyrazoles: From Synthesis to Applications

2020

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“…To this sense, we strongly believe that the authentication of the organocopper(III) fluoride, [Cu III (CF 3 ) 3 F] -(1), along with its proven versatility in C-C and C-heteroatom bond formations, will open new avenues in Cu III chemistry and further applications exploiting the reactive behavior of 1 and analogous Cu III halides are to come in the next years. 46…”

Section: Extension To Aryl-cf 3 and C-heteroatom Couplingsmentioning

confidence: 99%

On the Existence and Relevance of Copper(III) Fluorides in Oxidative Trifluoromethylation

Nebra,

Joven-Sancho

2024

Synlett

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Numerous reports invoke CuIII-F intermediates engaging in oxidative cross-couplings mediated by low/mid valent copper and formal sources of “F+” oxidants. These elusive and typically instable CuIII fluorides have been rarely characterized or spectroscopically identified, making their existence and participation within catalytic cycles somehow questionable. We have authenticated a stable organocopper(III) fluoride that undergoes Csp−CF3 bond formation upon addition of silyl-capped alkynes following a 2e― CuIII/CuI redox shuttle. This finding strongly supports the intermediacy of CuIII fluorides in C−C coupling. We review herein the State of the Art about well-defined CuIII fluorides enabling cross-coupling reactions.

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“…More recently, α-fluorinated nitroalkenes have been employed as synthetic equivalents of fluoroalkynes for annulation reactions which afforded a variety of monofluorinated heterocycles. 8 Based on our previous studies, 9 we anticipated that the nitro group might serve as a traceless activating group and a directing group in cycloaddition reactions with di/trifluoromethylated hydrazonoyl chlorides. 10 Moreover, this synthetic disconnection would provide a straightforward and practical strategy for the construction of highly substituted and functionalized fluoroalkyl-substituted fluoropyrazoles.…”

Section: Introductionmentioning

confidence: 99%