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  1. Article ; Online: Arene C-H Amination with

    Nakayama, Kaii / Okada, Yohei

    The Journal of organic chemistry

    2023  Volume 88, Issue 9, Page(s) 5913–5922

    Abstract: Arene C-H aminations using catalytic amounts of a 2,3-dichloro-5,6-dicyano- ...

    Abstract Arene C-H aminations using catalytic amounts of a 2,3-dichloro-5,6-dicyano-
    Language English
    Publishing date 2023-04-25
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.3c00293
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  2. Article: Radical cation Diels-Alder reactions of arylidene cycloalkanes.

    Nakayama, Kaii / Kamiya, Hidehiro / Okada, Yohei

    Beilstein journal of organic chemistry

    2022  Volume 18, Page(s) 1100–1106

    Abstract: ... ...

    Abstract TiO
    Language English
    Publishing date 2022-08-25
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2192461-2
    ISSN 1860-5397
    ISSN 1860-5397
    DOI 10.3762/bjoc.18.112
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Redox-Tag-Guided Radical Cation Diels–Alder Reactions: Use of Enol Ethers as Dienophiles

    Morizumi, Haruka / Nakayama, Kaii / Kitano, Yoshikazu / Okada, Yohei

    Synlett

    2023  Volume 35, Issue 03, Page(s) 362–366

    Abstract: Although radical cation Diels–Alder reactions enable the formation of cyclohexene ring systems between electronically mismatched (both electron-rich) dienes and dienophiles, which is otherwise difficult or impossible to achieve under thermal conditions, ... ...

    Abstract Although radical cation Diels–Alder reactions enable the formation of cyclohexene ring systems between electronically mismatched (both electron-rich) dienes and dienophiles, which is otherwise difficult or impossible to achieve under thermal conditions, the substrate scope has been limited. Herein, we disclose that a radical cation Diels–Alder reaction using an enol ether as an electron-rich (and therefore oxidizable) dienophile is possible through a rationally designed redox tag strategy. Electrochemical and TiO 2 photochemical approaches are effective in driving the reaction, where both intermolecular and intramolecular electron transfers are the key.
    Keywords redox tag ; radical cation ; Diels–Alder reaction ; enol ether ; electrochemistry ; photochemistry
    Language English
    Publishing date 2023-08-29
    Publisher Georg Thieme Verlag KG
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2042012-2
    ISSN 1437-2096 ; 0936-5214
    ISSN (online) 1437-2096
    ISSN 0936-5214
    DOI 10.1055/a-2161-9607
    Database Thieme publisher's database

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  4. Article: Radical Cation [2+2] Cycloadditions Enabled by Surface-Assisted Pseudo-Intramolecular Electron Transfers

    Adachi, Sota / Maeta, Naoya / Nakayama, Kaii / Wang, Zimo / Hashimoto, Yasuhiro / Okada, Yohei

    Synthesis

    2023  Volume 55, Issue 18, Page(s) 3013–3018

    Abstract: Both intermolecular and intramolecular electron transfers can be the key in the determination of synthetic outcomes of photochemical and electrochemical reactions. Herein, we report dispersed TiO 2 nanoparticles in combination with methoxybenzene to be a ...

    Abstract Both intermolecular and intramolecular electron transfers can be the key in the determination of synthetic outcomes of photochemical and electrochemical reactions. Herein, we report dispersed TiO 2 nanoparticles in combination with methoxybenzene to be a unique heterogeneous photocatalyst for facilitating the formation of novel cyclobutanes. Although the mechanistic details are as yet unclear, the results described herein imply that methoxybenzene is adsorbed onto the TiO 2 surface, coming in close proximity to the forming cyclobutane radical cation, to realize a pseudo-intramolecular electron transfer between the species.
    Keywords radical cations ; [2+2] cycloaddition ; surface-assisted ; pseudo-intramolecular process ; electron transfer
    Language English
    Publishing date 2023-02-21
    Publisher Georg Thieme Verlag KG
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/a-2039-4825
    Database Thieme publisher's database

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  5. Article ; Online: TiO

    Okada, Yohei / Maeta, Naoya / Nakayama, Kaii / Kamiya, Hidehiro

    The Journal of organic chemistry

    2018  Volume 83, Issue 9, Page(s) 4948–4962

    Abstract: Since the pioneering work by Macmillan, Yoon, and Stephenson, homogeneous photoredox catalysis has occupied a central place in new reaction development in the field of organic chemistry. While heterogeneous semiconductor photocatalysis has also been ... ...

    Abstract Since the pioneering work by Macmillan, Yoon, and Stephenson, homogeneous photoredox catalysis has occupied a central place in new reaction development in the field of organic chemistry. While heterogeneous semiconductor photocatalysis has also been studied extensively, it has generally been recognized as a redox option in inorganic chemistry where such "photocatalysis" is most often used to catalyze carbon-carbon bond cleavage and not in organic chemistry where bond formation is usually the focal point. Herein, we demonstrate that titanium dioxide photocatalysis is a powerful redox option to construct carbon-carbon bonds by using intermolecular formal [2 + 2] cycloadditions as models. Synergy between excited electrons and holes generated upon irradiation is expected to promote the overall net redox neutral process. Key for the successful application is the use of a lithium perchlorate/nitromethane electrolyte solution, which exhibits remarkable Lewis acidity to facilitate the reactions of carbon-centered radical cations with carbon nucleophiles. The reaction mechanism is reasonably understood based on both intermolecular and intramolecular single electron transfer regulated by an aromatic "redox tag". Most of the reactions were completed in less than 30 min even in aqueous and/or aerobic conditions without the need for sacrificial reducing or oxidizing substrates generally required for homogeneous photoredox catalysis.
    Language English
    Publishing date 2018--04
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.8b00738
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  6. Article ; Online: Radical Cation Diels-Alder Reactions by TiO

    Nakayama, Kaii / Maeta, Naoya / Horiguchi, Genki / Kamiya, Hidehiro / Okada, Yohei

    Organic letters

    2019  Volume 21, Issue 7, Page(s) 2246–2250

    Abstract: Radical cation Diels-Alder reactions by titanium dioxide ( ... ...

    Abstract Radical cation Diels-Alder reactions by titanium dioxide (TiO
    Language English
    Publishing date 2019-03-27
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.9b00526
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article: Radical Cation Diels–Alder Reactions by TiO₂ Photocatalysis

    Nakayama, Kaii / Naoya Maeta / Genki Horiguchi / Hidehiro Kamiya / Yohei Okada

    Organic letters. 2019 Mar. 27, v. 21, no. 7

    2019  

    Abstract: Radical cation Diels–Alder reactions by titanium dioxide (TiO₂) photocatalysis in lithium perchlorate/nitromethane solution are described. TiO₂ photocatalysis promotes reactions between electron-rich dienes and dienophiles, which would otherwise be ... ...

    Abstract Radical cation Diels–Alder reactions by titanium dioxide (TiO₂) photocatalysis in lithium perchlorate/nitromethane solution are described. TiO₂ photocatalysis promotes reactions between electron-rich dienes and dienophiles, which would otherwise be difficult to accomplish due to electronic mismatching. The reactions are triggered by hole oxidation of the dienophile and are completed by the excited electron reduction of the radical cation intermediate at the dispersed surface in the absence of any sacrificial substrate.
    Keywords cations ; chemical structure ; cycloaddition reactions ; lithium ; organic compounds ; oxidation ; perchlorates ; photocatalysis ; titanium dioxide
    Language English
    Dates of publication 2019-0327
    Size p. 2246-2250.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.9b00526
    Database NAL-Catalogue (AGRICOLA)

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