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  1. Article ; Online: [Exhaustive Syntheses of Deuterium-labelled Compounds].

    Sawama, Yoshinari

    Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan

    2022  Volume 142, Issue 2, Page(s) 139–144

    Abstract: Deuterium ( ...

    Abstract Deuterium (
    MeSH term(s) 2-Propanol/chemistry ; Alkenes/chemical synthesis ; Alkynes/chemical synthesis ; Alkynes/chemistry ; Amines/chemical synthesis ; Carbon/chemistry ; Catalysis ; Chemistry, Organic/methods ; Deuterium/chemistry ; Drug Development/methods ; Ethylamines/chemistry ; Gases ; Methane/analogs & derivatives ; Methane/chemistry ; Molecular Imaging/methods ; Nitriles/chemical synthesis ; Nitriles/chemistry ; Nitroparaffins/chemistry ; Palladium/chemistry ; Platinum/chemistry ; Solvents
    Chemical Substances Alkenes ; Alkynes ; Amines ; Ethylamines ; Gases ; Nitriles ; Nitroparaffins ; Solvents ; Platinum (49DFR088MY) ; Palladium (5TWQ1V240M) ; Carbon (7440-44-0) ; Deuterium (AR09D82C7G) ; dicyanmethane (EBL1KKS93J) ; 2-Propanol (ND2M416302) ; Methane (OP0UW79H66) ; nitromethane (RU5WG8C3F4) ; triethylamine (VOU728O6AY)
    Language Japanese
    Publishing date 2022-02-02
    Publishing country Japan
    Document type Journal Article
    ZDB-ID 200514-1
    ISSN 1347-5231 ; 0031-6903 ; 0372-7750 ; 0919-2085 ; 0919-2131
    ISSN (online) 1347-5231
    ISSN 0031-6903 ; 0372-7750 ; 0919-2085 ; 0919-2131
    DOI 10.1248/yakushi.21-00173-2
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Furanyl bis(indolyl)methane as a palladium ion-selective chromogenic agent.

    Ban, Kazuho / Nozaki, Shiho / Aijima, Takaaki / Oyama, Shuki / Tsujino, Hirofumi / Kanematsu, Yusuke / Akai, Shuji / Sawama, Yoshinari

    Organic & biomolecular chemistry

    2024  Volume 22, Issue 14, Page(s) 2734–2738

    Abstract: The colorless solution of furan-2-yl bis(indolyl)methane (BIM) is newly revealed to work as a palladium ( ... ...

    Abstract The colorless solution of furan-2-yl bis(indolyl)methane (BIM) is newly revealed to work as a palladium (Pd
    Language English
    Publishing date 2024-04-03
    Publishing country England
    Document type Journal Article
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d4ob00046c
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Arylation of indoles using cyclohexanones dually-catalyzed by niobic acid and palladium-on-carbons.

    Ban, Kazuho / Yamamoto, Yuta / Sajiki, Hironao / Sawama, Yoshinari

    Organic & biomolecular chemistry

    2020  Volume 18, Issue 20, Page(s) 3898–3902

    Abstract: 3-Arylindoles were easily constructed from indoles and cyclohexanone derivatives using a combination of catalytic niobic acid-on-carbon ( ... ...

    Abstract 3-Arylindoles were easily constructed from indoles and cyclohexanone derivatives using a combination of catalytic niobic acid-on-carbon (Nb
    Language English
    Publishing date 2020-05-12
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2097583-1
    ISSN 1477-0539 ; 1477-0520
    ISSN (online) 1477-0539
    ISSN 1477-0520
    DOI 10.1039/d0ob00702a
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Oxidative two-way regiocontrolled coupling of 3-methoxycarbonylcatechol and indoles to arylindoles.

    Sawama, Yoshinari / Kuwata, Shoko / Mae, Miyu / Udagawa, Taro / Akai, Shuji / Sajiki, Hironao

    Chemical communications (Cambridge, England)

    2022  Volume 58, Issue 93, Page(s) 12935–12938

    Abstract: 3-Methoxycarbonylcatechol effectively underwent two-way regiocontrolled coupling with ... ...

    Abstract 3-Methoxycarbonylcatechol effectively underwent two-way regiocontrolled coupling with indoles
    MeSH term(s) Indoles ; Oxidation-Reduction ; Oxidative Stress
    Chemical Substances Indoles
    Language English
    Publishing date 2022-11-22
    Publishing country England
    Document type Journal Article
    ZDB-ID 1472881-3
    ISSN 1364-548X ; 1359-7345 ; 0009-241X
    ISSN (online) 1364-548X
    ISSN 1359-7345 ; 0009-241X
    DOI 10.1039/d2cc04843d
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Oxidative Functionalization of Catechol Derivatives Substituted with Electron-Withdrawing Groups.

    Sawama, Yoshinari / Shimizu, Hyoga / Aijima, Takaaki / Udagawa, Taro / Kuwata, Shoko / Yamada, Tsuyoshi / Sajiki, Hironao / Akai, Shuji

    Chemical & pharmaceutical bulletin

    2023  Volume 71, Issue 10, Page(s) 782–786

    Abstract: Catechols possessing electron-withdrawing groups at the C3 position effectively underwent oxidative functionalization at the C4 position in the presence of phenyliodine(III) diacetate (PIDA) and heteroarene nucleophiles (e.g., indole, indazole, and ... ...

    Abstract Catechols possessing electron-withdrawing groups at the C3 position effectively underwent oxidative functionalization at the C4 position in the presence of phenyliodine(III) diacetate (PIDA) and heteroarene nucleophiles (e.g., indole, indazole, and benzotriazole) to produce the corresponding biaryl products. The PIDA-mediated oxidation of catechol derivatives afforded the ortho-benzoquinone intermediate, which subsequently underwent regioselective nucleophilic addition to the α,β-unsaturated carbonyl moiety of ortho-benzoquinone using indole, indazole, and benzotriazole to give 4-substituted catechol derivatives in a one-pot manner. Notably, the nucleophilic substitution positions of indazole and benzotriazole were perfectly controlled. Additionally, the reaction using N-methylaniline as the nucleophile afforded a tertiary amine product.
    MeSH term(s) Electrons ; Catechols ; Benzoquinones ; Oxidative Stress
    Chemical Substances catechol (LF3AJ089DQ) ; Catechols ; Benzoquinones
    Language English
    Publishing date 2023-09-16
    Publishing country Japan
    Document type Journal Article
    ZDB-ID 213307-6
    ISSN 1347-5223 ; 0009-2363
    ISSN (online) 1347-5223
    ISSN 0009-2363
    DOI 10.1248/cpb.c23-00493
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

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  6. Article ; Online: Sulfonium Salt Reagents for the Introduction of Deuterated Alkyl Groups in Drug Discovery.

    Ban, Kazuho / Imai, Keisuke / Oyama, Shuki / Tokunaga, Jin / Ikeda, Yui / Uchiyama, Hiromasa / Kadota, Kazunori / Tozuka, Yuichi / Akai, Shuji / Sawama, Yoshinari

    Angewandte Chemie (International ed. in English)

    2023  Volume 62, Issue 48, Page(s) e202311058

    Abstract: The pharmacokinetics of pharmaceutical drugs can be improved by replacing C-H bonds with the more stable C-D bonds at the α-position to heteroatoms, which is a typical metabolic site for cytochrome P450 enzymes. However, the application of deuterated ... ...

    Abstract The pharmacokinetics of pharmaceutical drugs can be improved by replacing C-H bonds with the more stable C-D bonds at the α-position to heteroatoms, which is a typical metabolic site for cytochrome P450 enzymes. However, the application of deuterated synthons is limited. Herein, we established a novel concept for preparing deuterated reagents for the successful synthesis of complex drug skeletons with deuterium atoms at the α-position to heteroatoms. (d
    MeSH term(s) Deuterium/chemistry ; Salts ; Cytochrome P-450 Enzyme System ; Sodium Chloride ; Drug Discovery
    Chemical Substances Deuterium (AR09D82C7G) ; Salts ; Cytochrome P-450 Enzyme System (9035-51-2) ; Sodium Chloride (451W47IQ8X)
    Language English
    Publishing date 2023-09-27
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202311058
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article: Gold-Catalyzed Tandem Oxidative Coupling Reaction between β-Ketoallenes and Electron-Rich Arenes to 2-Furylmethylarenes

    Yasukawa, Naoki / Yamada, Yutaro / Furugen, Chikara / Miki, Yuya / Sajiki, Hironao / Sawama, Yoshinari

    Organic letters. 2021 July 28, v. 23, no. 15

    2021  

    Abstract: A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl₃ and phenyliodine diacetate. The Auᴵᴵᴵ salt catalyzed the cyclization of β-ketoallenes to form a 2-furylmethyl ... ...

    Abstract A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl₃ and phenyliodine diacetate. The Auᴵᴵᴵ salt catalyzed the cyclization of β-ketoallenes to form a 2-furylmethyl gold intermediate, and the subsequent C–H functionalization of arenes proceeded smoothly. During the oxidative coupling, nucleophilic additions occurred at the center and terminal carbon atoms of the allene moiety to form C–O and C–C bonds.
    Keywords Lewis bases ; allene ; carbon ; carbon-hydrogen bond activation ; gold ; iodobenzenes ; moieties
    Language English
    Dates of publication 2021-0728
    Size p. 5891-5895.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.1c02007
    Database NAL-Catalogue (AGRICOLA)

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  8. Article ; Online: Copper-Catalyzed Aqueous N-O Bond Cleavage of 2-Oxa-3-Azabicyclo Compounds to Cyclic cis-1,4-Amino Alcohols.

    Yasukawa, Naoki / Miki, Yuya / Kuwata, Marina / Sajiki, Hironao / Sawama, Yoshinari

    ChemSusChem

    2020  Volume 13, Issue 21, Page(s) 5632–5637

    Abstract: The N-O bond cleavage of 2-oxa-3-azabicyclo substrates, which are readily prepared by the hetero Diels-Alder reaction between nitroso dienophiles and cyclic 1,3-dienes, was effectively catalyzed by heterogeneous copper-on-carbon (Cu/C) under aqueous ... ...

    Abstract The N-O bond cleavage of 2-oxa-3-azabicyclo substrates, which are readily prepared by the hetero Diels-Alder reaction between nitroso dienophiles and cyclic 1,3-dienes, was effectively catalyzed by heterogeneous copper-on-carbon (Cu/C) under aqueous conditions to give the corresponding cyclic cis-1,4-amino alcohol derivatives. The present method was applied to the direct incorporation of the hydroxy and amino groups derived from a nitroso substrate into cyclic 1,3-dienes with cis-selectivity by the combination of the in situ formation of 2-oxa-3-azabicyclo compounds and following Cu/C-catalyzed N-O bond cleavage. The obtained cis-4-aminocyclohexenols, derived from cyclohexadiene as a cyclic 1,3-diene, could be selectively oxidized by using the ruthenium-on-carbon (Ru/C) catalyst under oxygen atmosphere to the corresponding 4-aminocyclohexenones at 50-65 °C or para-iminoquinones at 100-110 °C as useful reactive synthetic precursors.
    Language English
    Publishing date 2020-09-09
    Publishing country Germany
    Document type Journal Article
    ISSN 1864-564X
    ISSN (online) 1864-564X
    DOI 10.1002/cssc.202001739
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article ; Online: Gold-Catalyzed Tandem Oxidative Coupling Reaction between β-Ketoallenes and Electron-Rich Arenes to 2-Furylmethylarenes.

    Yasukawa, Naoki / Yamada, Yutaro / Furugen, Chikara / Miki, Yuya / Sajiki, Hironao / Sawama, Yoshinari

    Organic letters

    2021  Volume 23, Issue 15, Page(s) 5891–5895

    Abstract: A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using ... ...

    Abstract A tandem oxidative coupling reaction of β-ketoallenes and arenes was developed, which leads to the formation of 2-furylmethylarenes using AuCl
    Language English
    Publishing date 2021-07-28
    Publishing country United States
    Document type Journal Article
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.1c02007
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  10. Article ; Online: New Gateways to the Platinum Group Metal-Catalyzed Direct Deuterium-Labeling Method Utilizing Hydrogen as a Catalyst Activator.

    Sawama, Yoshinari / Park, Kwihwan / Yamada, Tsuyoshi / Sajiki, Hironao

    Chemical & pharmaceutical bulletin

    2018  Volume 66, Issue 1, Page(s) 21–28

    Abstract: Deuterium-labeled compounds are widely utilized in various scientific fields. We summarize the recent advances in the direct deuteration of sugar, saturated fatty acid, and arene derivatives using heterogeneous platinum group metal on carbon catalysts by ...

    Abstract Deuterium-labeled compounds are widely utilized in various scientific fields. We summarize the recent advances in the direct deuteration of sugar, saturated fatty acid, and arene derivatives using heterogeneous platinum group metal on carbon catalysts by our research group. Hydrogen gas is a key catalyst-activator to facilitate the present H-D exchange reactions. In this review, the direct activation method of catalysts using in situ-generated hydrogen based on the dehydrogenation of alcohols is introduced. The obtained multiple deuterium-labeled products, including bioactive compounds, are expected to contribute to the development of many scientific investigations.
    MeSH term(s) Alcohols/chemistry ; Catalysis ; Deuterium/chemistry ; Hydrogen/chemistry ; Metals, Heavy/chemistry ; Molecular Structure ; Organometallic Compounds/chemistry
    Chemical Substances Alcohols ; Metals, Heavy ; Organometallic Compounds ; Hydrogen (7YNJ3PO35Z) ; Deuterium (AR09D82C7G)
    Language English
    Publishing date 2018
    Publishing country Japan
    Document type Journal Article ; Review
    ZDB-ID 213307-6
    ISSN 1347-5223 ; 0009-2363
    ISSN (online) 1347-5223
    ISSN 0009-2363
    DOI 10.1248/cpb.c17-00222
    Database MEDical Literature Analysis and Retrieval System OnLINE

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