Synthesis and insecticidal activity of fluorinated 2-(2,6-dichloro-4-trifluoromethylphenyl)-2,4,5,6-tetrahydrocyclopentapyrazoles

Meegalla, Sanath K.; Doller, Darı́o; Liu, Ruiping; Sha, Deyou; Lee, Yu-Kai; Söll, Richard; Wisnewski, Nancy; Silver, Gary M.; Dhanoa, Dale

doi:10.1016/j.bmcl.2005.12.012

Cited by 12 publications

(7 citation statements)

References 3 publications

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“…Such approaches often display poor stereoselectivity or result in rearrangement products. Treatment of 1,2-diols with SF 4 [22–23], DAST [24], or deoxofluor [25] also leads to vicinal difluorides. Reaction with vicinal triflates has also been successful in some cases [7,26].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

Linclau¹,

Leung²,

Nonnenmacher³

et al. 2010

Beilstein J. Org. Chem.

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SummaryA large-scale synthesis of meso-2,3-difluoro-1,4-butanediol in 5 steps from (Z)-but-2-enediol is described. Crystallographic analysis of the diol and the corresponding benzyl ether reveals an anti conformation of the vicinal difluoride moiety. Monosilylation of the diol is high-yielding but all attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed.

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Section: Introductionmentioning

confidence: 99%

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

Linclau¹,

Leung²,

Nonnenmacher³

et al. 2010

Beilstein J. Org. Chem.

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“…It was reported that α,α-difluorocyclopentanones could be prepared via the fluorinations of the corresponding cyclopentanones (Scheme 1A), including either by a direct nucleophilic α-fluorination 5b,7 or by a deoxygenative fluorination−oxidation sequence. 8 This kind of strategy requires the preconstruction of a cyclopentanone skeleton and usually suffers from hazardous fluorinating reagents. Moreover, the regioselectivity of the fluorination, in the case of those cyclopentanones bearing multiple reaction sites as the substrates, still remains a challenging issue.…”

mentioning

confidence: 99%

“…However, current work is limited to the construction of difluorinated ketone scaffolds. ,, A facile and efficient approach for the synthesis of cyclic analogs has not been established. It was reported that α,α-difluorocyclopentanones could be prepared via the fluorinations of the corresponding cyclopentanones (Scheme A), including either by a direct nucleophilic α-fluorination , or by a deoxygenative fluorination–oxidation sequence . This kind of strategy requires the preconstruction of a cyclopentanone skeleton and usually suffers from hazardous fluorinating reagents.…”

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confidence: 99%

Me₃SiCF₂Br-Self-Assisted Domino Reaction: Catalytic Synthesis of α,α-Difluorocyclopentanones from Methylvinylketones

Chang

Gao

et al. 2017

Org. Lett.

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A complete self-assistance strategy based on MeSiCFBr was used in the domino conversion of methylvinylketones into α,α-difluorinated cyclopentanones. Initiated by 5 mol % of nBuNBr, the multistep reaction occurred in one pot under mild conditions via the in situ formation of silyl dienol ethers, difluorocyclopropanation, thermal vinylcyclopropane-cyclopentene rearrangement, and desilylation. The process takes advantage of the multitasking capability of MeSiCFBr as the difluorocarbene source, a silicon-based transfer agent, and a bromine anion releaser.

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“…Phenylpyrazoles are an important class of heterocycles that are present in many natural products and pharmaceutical intermediates . Moreover, phenylpyrazole derivatives containing fluorine groups have been found to exhibit a broad range of biological activities . For example, the commercial fipronil ( I , Fig.…”

Section: Introductionmentioning

confidence: 99%

The Synthesis of Fipronil Derivatives via Pd‐Catalyzed Direct Alkynylation of Phenylpyrazole with Terminal Alkynes in Green Solvents

Chen

Zhang

2016

Journal of Heterocyclic Chem

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The palladium‐catalyzed direct alkynylation of phenylpyrazole (5‐amino‐1‐[2, 6‐dichloro‐4‐trifluoromethylphenyl]‐lH‐pyrazole‐3‐carbonitrile) with terminal alkynes is being reported. The protocol utilizes EtOH/H2O as the solvents and does not require the preactivation of phenylpyrazole with halide to form its halide substrate, which exemplifies the ideal condition of green chemistry. Various terminal alkynes such as arylacetylenes and aliphatic alkynes are used in the reaction to afford a series of fipronil derivatives of 4‐alkynyl‐1‐phenylpyrazoles with potential bioactivity in good yields. All the compounds were characterized by 1H NMR, 13C NMR, and HRMS spectroscopic techniques.

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Synthesis and insecticidal activity of fluorinated 2-(2,6-dichloro-4-trifluoromethylphenyl)-2,4,5,6-tetrahydrocyclopentapyrazoles

Cited by 12 publications

References 3 publications

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

Me₃SiCF₂Br-Self-Assisted Domino Reaction: Catalytic Synthesis of α,α-Difluorocyclopentanones from Methylvinylketones

The Synthesis of Fipronil Derivatives via Pd‐Catalyzed Direct Alkynylation of Phenylpyrazole with Terminal Alkynes in Green Solvents

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Synthesis and insecticidal activity of fluorinated 2-(2,6-dichloro-4-trifluoromethylphenyl)-2,4,5,6-tetrahydrocyclopentapyrazoles

Cited by 12 publications

References 3 publications

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane

Me3SiCF2Br-Self-Assisted Domino Reaction: Catalytic Synthesis of α,α-Difluorocyclopentanones from Methylvinylketones

The Synthesis of Fipronil Derivatives via Pd‐Catalyzed Direct Alkynylation of Phenylpyrazole with Terminal Alkynes in Green Solvents

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Me₃SiCF₂Br-Self-Assisted Domino Reaction: Catalytic Synthesis of α,α-Difluorocyclopentanones from Methylvinylketones