Copper(II)‐Catalysed Aerobic Oxidative Coupling of Arylamines with Hexafluoroisopropanol: An Alternative Methodology for Constructing Fluorinated Compounds

Wu, Liangying; Yang, Song; Li, Zhanchong; Guo, Jiabao; Yao, Xiaoquan

doi:10.1002/adsc.202001048

Cited by 8 publications

(3 citation statements)

References 56 publications

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“…Compared with the 19 F NMR spectra of HFIP, a new singlet at −82.6 ppm (s) appeared, which was known as hexafluoroacetone (see the Supporting Information). Therefore, it could be proved that HFIP participated in the redox reaction.…”

Section: Resultsmentioning

confidence: 99%

Direct para-Selective C–H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

et al. 2021

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Iodine(III)-mediated synthesis of 4-iodo-N-phenylaniline from iodobenzene has been achieved, and the reaction can proceed under mild conditions. A variety of functional groups were well tolerated, providing the corresponding products in moderate to good yields. The remaining iodine group provides an effective platform for converting the products into several valuable asymmetric diphenylamines. Most importantly, this reaction can be easily scaled up to the ten-gram scale, highlighting its synthetic utility. The mechanistic study revealed that the in situ generated aryl hypervalent iodine intermediate is the key factor to realize this para-selective C–H amination reaction.

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Section: Resultsmentioning

confidence: 99%

Direct para-Selective C–H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

et al. 2021

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“…Arylamines and their derivatives possess a paramount importance as intermediates for pharmaceuticals and natural products, agrochemicals, conducting polymers (PANI), and dyes in the chemical industry. [54][55][56] Arylamines are extremely important ligand for the coordination to transition metals. 57 The Buchwald-Hartwig coupling of amines and aryl halides in the presence of Pd is a great method for the preparation of arylamines.…”

Section: C-n Cross-coupling Reaction Catalyzed By -Fe2o3@mbd/pd-co In Watermentioning

confidence: 99%

A New Nanomagnetic Pd-Co Bimetallic Alloy as Catalyst in the Mizoroki-Heck and Buchwald–Hartwig Amination Reactions in Aqueous Media

Sobhani

Zarei

Sansano

2021

Preprint

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A Pd-Co bimetallic alloy encapsulated in melamine-based dendrimer supported on magnetic nanoparticles denoted as γ-Fe2O3@MBD/Pd-Co was synthesized by a facile co-complexation-reduction method and characterized sufficiently. The catalytic evaluation of γ-Fe2O3@MBD/Pd-Co showed promising results in the Mizoroki-Heck and Buchwald-Hartwig amination reactions of various iodo-, bromo- and challenging chloroarenes in aqueous media. The synergetic cooperative effect of both Pd and Co and dispersion of the catalyst in water due to the encapsulation of γ-Fe2O3 by melamine-based dendrimer lead to high catalytic performance compared with the monometallic counterparts. The dispersion of the magnetic catalyst also facilitates the recovery and reuse of the catalyst by ten consecutive extraction and final magnetic isolation with no loss of catalytic activity, keeping its structure unaltered. Remarkably, this is the first paper on the use of palladium-cobalt bimetallic catalyst for Buchwald-Hartwig amination reaction and the first magnetically recyclable Pd/Co bimetallic catalyst in the Mizoroki-Heck coupling reactions.

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“…electrophilic, nucleophilic, and radical addition . In spite of the medicinal importance of hydroxyfluoroalkylated molecules, the reports on hydroxyfluoroalkyl incorporation into different bioactive organic scaffolds is still limited. ,, The Liu group demonstrated the application of a cross-dehydrogenative coupling strategy to efficiently introduce the hydroxyfluoroalkyl group into organic molecules by utilizing polyfluoroalkyl alcohols (Scheme a) . Further, Kumar and co-workers reported a radical hydroxyfluoroalkylation of indoles with fluoroalkyl alcohols using TEMPO under thermal conditions (Scheme b) …”

Section: Introductionmentioning

confidence: 99%

Photoredox Minisci-Type Hydroxyfluoroalkylation of Isoquinolines with N-Trifluoroethoxyphthalimide

et al. 2023

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A straightforward photocatalytic approach has been demonstrated to incorporate a trifluoroethanol unit onto the isoquinolines. Herein, we report N-trifluoroethoxyphthalimide as a hydroxyfluoroalkyl radical precursor, enabling efficient synthesis of trifluoroethanol-substituted heteroarenes. Radical quenching experiments confirmed the involvement of a free-radical pathway under developed photocatalytic conditions. The DFT calculations confirmed the intramolecular 1,2-HAT reactivity of the Ocentered trifluoroethoxy radical (generated from N-trifluoroethoxyphthalimide under photocatalytic condition) to the C-centered trifluoroethanol radical. Fluorescence quenching studies suggested that isoquinoline was responsible for the quenching of Irphotocatalyst emission. A catalytic cycle involving trifluoroethanol radical reaction with isoquinolines has been proposed.

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Copper(II)‐Catalysed Aerobic Oxidative Coupling of Arylamines with Hexafluoroisopropanol: An Alternative Methodology for Constructing Fluorinated Compounds

Cited by 8 publications

References 56 publications

Direct para-Selective C–H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

Direct para-Selective C–H Amination of Iodobenzenes: Highly Efficient Approach for the Synthesis of Diarylamines

A New Nanomagnetic Pd-Co Bimetallic Alloy as Catalyst in the Mizoroki-Heck and Buchwald–Hartwig Amination Reactions in Aqueous Media

Photoredox Minisci-Type Hydroxyfluoroalkylation of Isoquinolines with N-Trifluoroethoxyphthalimide

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