Benzylic C(sp<sup>3</sup>)H Perfluoroalkylation of Six‐Membered Heteroaromatic Compounds

Kuninobu, Yoichiro; Nagase, Masahiro; Kanai, Motomu

doi:10.1002/ange.201505335

Cited by 17 publications

(3 citation statements)

References 52 publications

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“…Introduction of a carboxyl group sufficiently improved the water solubility of the catalysts. Moreover, catalysts 6 and 7 contained a fluoro perfluoroalkylboron group [22][23][24] at the electron-acceptor moiety, a stronger electron-withdrawing group than a difluoroboron group of 5.…”

Section: Design and Properties Of Photooxygenation Catalystsmentioning

confidence: 99%

Near-Infrared Photoactivatable Oxygenation Catalysts of Amyloid Peptide

Taniguchi

Ozawa

et al. 2018

Chem

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A biocompatible photooxygenation catalyst that can selectively oxygenate and degrade the pathogenic aggregation of Alzheimer's disease (AD)-related amyloid-b peptide (Ab) under near-infrared light irradiation has been developed. The catalyst oxygenates Ab embedded under the skin of a living mouse and diminishes the intact Ab level in an AD-model mouse brain. The new catalyst is potentially applicable for the treatment of peripheral amyloid diseases and AD.

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Section: Design and Properties Of Photooxygenation Catalystsmentioning

confidence: 99%

Near-Infrared Photoactivatable Oxygenation Catalysts of Amyloid Peptide

Taniguchi

Ozawa

et al. 2018

Chem

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“…2c). Remarkably, direct Csp3 C-H trifluoromethylation occurs at Gly, Ala, Val, Ile, and Leu, showing a unique trifluoromethylation without Lewis-acid catalysis [20] or a cross-dehydrogenative coupling (CDC). [21] Given that the side chains of Gly, Ala, Ser, Thr, Asp, Glu are relatively •OH silent, •CF 3 fulfills our goal to complement OH footprinting with a broadly reactive reagent with widely different properties.…”

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confidence: 99%

Laser‐Initiated Radical Trifluoromethylation of Peptides and Proteins: Application to Mass‐Spectrometry‐Based Protein Footprinting

et al. 2017

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We describe a novel, laser-initiated radical trifluoromethylation for protein footprinting and establish its broad residue coverage. •CF3 reacts with 18 of 20 common amino acids including Gly, Ala, Ser, Thr, Asp, Glu that are relatively “silent” with •OH. This new approach to footprinting is a bridge between trifluoromethylation in materials and medicinal chemistry and structural biology and biotechnology. Its application to a membrane protein and to myoglobin show that the approach is sensitive to protein conformational change and solvent accessibility.

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“…After screening the reaction conditions, 2‐(2,2,2‐trifluoroethyl)quinoline was obtained with an 85 % yield on a gram scale (Scheme 6). [11] Using this method, perfluoroalkyl groups, such as pentafluoroethyl and heptafluoropropyl, can be introduced at the benzylic position of 2‐methylquinoline. The reaction also proceeded at the internal benzylic position.…”

Section: Electrophilic Activation Of Six‐membered Heteroaromatic Ringsmentioning

confidence: 99%

Regioselective C−H Trifluoromethylation and Its Related Reactions of (Hetero)aromatic Compounds

Kuninobu

2023

The Chemical Record

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Fluorinated functional groups, including trifluoromethyl group, play important roles in the development of drugs, agrochemicals, and organic functional materials. Therefore, the development of highly effective and practical reactions to introduce fluorinated functional groups into (hetero)aromatic compounds is highly desirable. We have achieved several regioselective C−H trifluoromethylation and related reactions by electrophilic and nucleophilic activation of six‐membered heteroaromatic compounds and steric protection of aromatic compounds. These reactions proceed in good to excellent yields, even on a gram scale, with high functional group tolerance, and are applicable to the regioselective trifluoromethylation of drug molecules. In this personal account, the background of the introduction reactions of fluorinated functional groups, our reaction designs to achieve regioselective C−H trifluoromethylation and the related reactions of (hetero)aromatic compounds are explained.

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Benzylic C(sp³)H Perfluoroalkylation of Six‐Membered Heteroaromatic Compounds

Abstract: Successful benzylic C(sp 3 ) À Ht rifluoromethylation, pentafluoroethylation, and heptafluoropropylation of sixmembered heteroaromatic compounds were achieved

Cited by 17 publications

References 52 publications

Near-Infrared Photoactivatable Oxygenation Catalysts of Amyloid Peptide

Near-Infrared Photoactivatable Oxygenation Catalysts of Amyloid Peptide

Laser‐Initiated Radical Trifluoromethylation of Peptides and Proteins: Application to Mass‐Spectrometry‐Based Protein Footprinting

Regioselective C−H Trifluoromethylation and Its Related Reactions of (Hetero)aromatic Compounds

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Benzylic C(sp3)H Perfluoroalkylation of Six‐Membered Heteroaromatic Compounds

Abstract: Successful benzylic C(sp 3 ) À Ht rifluoromethylation, pentafluoroethylation, and heptafluoropropylation of sixmembered heteroaromatic compounds were achieved

Cited by 17 publications

References 52 publications

Near-Infrared Photoactivatable Oxygenation Catalysts of Amyloid Peptide

Near-Infrared Photoactivatable Oxygenation Catalysts of Amyloid Peptide

Laser‐Initiated Radical Trifluoromethylation of Peptides and Proteins: Application to Mass‐Spectrometry‐Based Protein Footprinting

Regioselective C−H Trifluoromethylation and Its Related Reactions of (Hetero)aromatic Compounds

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Benzylic C(sp³)H Perfluoroalkylation of Six‐Membered Heteroaromatic Compounds