Nagoya University · Materials Science
Professor Naoki Noto's research lab specializes in the development of sustainable and selective photoredox catalysis for the synthesis of fluorinated organic compounds. The lab focuses on metal-free, visible-light-driven transformations that enable the efficient introduction of fluorinated groups—such as CF₃, CF₂H, and CH₂F—into complex molecular architectures with high regio- and diastereoselectivity. Key innovations include the design of novel photocatalysts and fluorinated reagents that operate under mild conditions, expanding access to valuable fluorinated building blocks for pharmaceuticals and agrochemicals. The lab also pioneers supramolecular approaches to enhance catalytic efficiency in aqueous media, advancing green chemistry principles in fluorination reactions.
Figures are computed from collected data and may differ slightly.
Regioselective amino-difluoromethylation of aromatic alkenes <i>via</i> C(sp<sup>3</sup>)-CF<sub>2</sub>H and C(sp<sup>3</sup>)-N bond formation with the C[double bond, length as m-dash]C moiety has been achieved in a single operation by visible-light photoredox catalysis. The combination of a shelf-stable and easy-to-handle sulfonium salt, <i>S</i>-difluoromethyl-<i>S</i>-di(<i>p</i>-xylyl)sulfonium tetrafluoroborate, and perylene catalysis is the key to the successful transformation. Furthermo
Monofluoromethyl (CH2F) radical can be easily generated from a sulfoximine-based precursor (CH2F–S(=O)(=NTs)-Ph) by the action of visible-light metal-free photoredox catalysis with readily accessible 1,4-bis(diphenylamino)naphthalene. The catalyst design based on the high excitation energy (E0,0) and interchromophoric conjugation features a strong reducing power and a high quantum yield of emission of the photocatalyst. In addition, their photophysical properties are preserved in various polar s
A novel synthesis of CF3-containing spirooxazolines and spirooxazines has been developed. Regiospecific trifluoromethylative spirocyclization (CF3-spirocyclization) of cyclic alkenes bearing an amide pendant mediated by photoredox catalysis is a useful strategy for construction of a C(sp(3))-CF3 bond and an spirooxazoline or spirooxazine ring onto C═C bonds via a single step. The key intermediate is α-CF3-substituted carbocationic species smoothly generated from single-electron-transfer (SET) ph
Well-defined 9,10-bis(di(p-tert-butylphenyl)amino)anthracene serves as a photocatalyst for radical fluoroalkylation under visible light irradiation. The diarylamine (Donor)–anthracene (π conjugated system)–diarylamine (Donor) scaffolds are easily accessed by typical palladium-catalyzed cross-coupling protocols of the corresponding halogenated anthracenes with various lithium diarylamides. The anthracene-based photocatalyst exhibits high reducing power, leading to generation of versatile fluoroal
Simple synthesis of CF3- and CF2H-spiroethers from aryl-fused cycloalkenylalkanols by photoredox catalysis has been developed. Modification of the fluoromethylating reagents and the photoredox catalysts leads to both CF3- and CF2H-spiroetherification. The present photocatalytic system allows us to access a variety of new anti-fluoromethylated spiroethers in a highly selective manner.
An organic reaction in water using visible light as the only energy source is one of the goals of modern synthetic organic chemistry, and the encapsulation of a photoredox catalyst by a water-soluble molecular capsule is a promising strategy for it. Herein, we report on a transition metal-free supramolecular catalyst composed of V-shaped aromatic amphiphiles and a phenoxazine photoredox catalyst. A nanosized molecular capsule can efficiently uptake an organic photoredox catalyst in water, and th
Organic photoredox catalysts (OPCs) have the potential to replace precious-metal-based photoredox catalysts (PMPCs). Compared with strongly oxidizing OPCs, such as the representative acridinium salts, however, the recent development of strongly reducing OPCs has been relatively sluggish. In this Perspective, strongly reducing OPCs bearing arylamine motifs are introduced. One of the advantages of OPCs is their versatility in catalyst design, which makes it easier to develop catalysts with a reduc
Catalytic systems using a small amount of organic photosensitizer for the activation of an inorganic (on-demand ligand-free) nickel(II) salt represent a cost-effective method for cross-coupling reactions, while C(sp<sup>2</sup> )-O bond formation remains less developed. Herein, we report a strategy for the synthesis of phenols with a nickel(II) salt and an organic photosensitizer, which was identified via an investigation into the catalytic activity of 60 organic photosensitizers consisting of v
Organic photoredox catalysis has become a useful tool for the development of metal-free radical reactions. Recently, we have reported that 1,4-bis(diphenylamino)naphthalene <b>N</b> serves as an efficient photoredox catalyst for radical monofluoromethylation with <i>N</i>-tosyl-<i>S</i>-monofluoromethyl-<i>S</i>-phenylsulfoximine <b>2</b>. In this paper, we report the preparation and photo- and electrochemical properties of (diarylamino)naphthalene derivatives, 1,4-bis(di(<i>p</i>-<i>tert</i>-bu
While seasoned organic chemists can often predict suitable catalysts for new reactions based on their past experiences in other catalytic reactions, developing this ability is costly, laborious and time-consuming. Therefore, replicating this remarkable expertize of human researchers through machine learning (ML) is compelling, albeit that it remains highly challenging. Herein, we apply a domain-adaptation-based transfer-learning (TL) approach to photocatalysis. Despite being different reaction t
During the recent development of machine-learning (ML) methods for organic synthesis, the value of "failed experiments" has increasingly been acknowledged. Accordingly, we have developed an exhaustive database comprising 300 entries of experimental data obtained by performing ruthenium-catalyzed hydrogenation reactions using 10 ketones as substrates and 30 phosphine ligands. After evaluating the predictive performance of ML models using the constructed database, we conducted a virtual screening
Abstract Catalytic systems using a small amount of organic photosensitizer for the activation of an inorganic (on‐demand ligand‐free) nickel(II) salt represent a cost‐effective method for cross‐coupling reactions, while C(sp 2 )−O bond formation remains less developed. Herein, we report a strategy for the synthesis of phenols with a nickel(II) salt and an organic photosensitizer, which was identified via an investigation into the catalytic activity of 60 organic photosensitizers consisting of va
Abstract Starting from cyclic alkenes bearing an amide tether the title reaction provides trifluoromethylated spirooxazolines or spirooxazines in moderate to high yields and with moderate to high anti‐diastereoselectivity.
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.
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