Synthesis of Unsymmetrical Diaryl Selenides: Copper-Catalyzed Se-Arylation of Diaryl Diselenides with Triarylbismuthanes

被引:15
|
作者
Matsumura, Mio [1 ]
Shibata, Kohki [1 ]
Ozeki, Sota [1 ]
Yamada, Mizuki [1 ]
Murata, Yuki [1 ]
Kakusawa, Naoki [2 ]
Yasuike, Shuji [1 ]
机构
[1] Aichi Gakuin Univ, Sch Pharmaceut Sci, Chikusa Ku, 1-100 Kusumoto Cho, Nagoya, Aichi 4648650, Japan
[2] Hokuriku Univ, Fac Pharmaceut Sci, Ho 3 Kanagawa Machi, Kanazawa, Ishikawa 9201181, Japan
来源
SYNTHESIS-STUTTGART | 2016年 / 48卷 / 05期
关键词
bismuthanes; diselenides; selenides; copper; catalysis; cross-coupling; BOND FORMATION; N-ARYLATION; DIPHENYL DISELENIDE; ARYLBORONIC ACIDS; ARYL HALIDES; C-SE; CONVENIENT SYNTHESIS; COUPLING REACTIONS; TE BOND; ORGANOSELENIUM;
D O I
10.1055/s-0035-1561280
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed C(aryl)-Se bond formation by the reaction of diaryl diselenides with triarylbismuthanes in the presence of copper(I) acetate (10 mol%) and 1,10-phenanthroline (10 mol%) under aerobic conditions led to the formation of unsymmetric diaryl selenides in moderate to excellent yields. This reaction proceeded efficiently; all three aryl groups in the bismuthane and both the selanyl groups in the diaryl diselenide were transferred to the coupling products.
引用
收藏
页码:730 / 736
页数:7
相关论文
共 50 条
  • [1] Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides
    Kobiki, Yohsuke
    Kawaguchi, Shin-ichi
    Ohe, Takashi
    Ogawa, Akiya
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1141 - 1147
  • [2] Atom-Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides
    Taniguchi, Toshihide
    Murata, Akinori
    Takeda, Motonori
    Mizuno, Takumi
    Nomoto, Akihiro
    Ogawa, Akiya
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (33) : 4928 - 4934
  • [3] Simple and efficient copper-catalyzed synthesis of symmetrical diaryl selenides from triarylbismuthanes and selenium under aerobic conditions
    Matsumura, Mio
    Kumagai, Hanae
    Murata, Yuki
    Kakusawa, Naoki
    Yasuike, Shuji
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2016, 807 : 11 - 16
  • [4] Simple and efficient copper-catalyzed S-arylation of diaryl disulfides with triarylbismuthanes under aerobic conditions
    Yasuike, Shuji
    Nishioka, Motokazu
    Kakusawa, Naoki
    Kurita, Jyoji
    TETRAHEDRON LETTERS, 2011, 52 (48) : 6403 - 6406
  • [5] Silver-Catalyzed Synthesis of Diaryl Selenides by Reaction of Diaryl Diselenides with Aryl Boronic Acids
    Goldani, Bruna
    Ricordi, Vanessa G.
    Seus, Natalia
    Lenardao, Eder J.
    Schumacher, Ricardo F.
    Alves, Diego
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 11472 - 11476
  • [6] Copper-catalyzed one-pot tandem synthesis of unsymmetrical diaryl selenides from two different aryl iodides
    Zhang, Shaozhong
    Koe, Adam
    Heintz, Christina
    Senior, Aunajay
    Gibson, Abigail
    Jin, Jin
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [7] New approaches to the synthesis of unsymmetrical diaryl selenides
    Beletskaya, IP
    Sigeev, AS
    Peregudov, AS
    Petrovskii, PV
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 605 (01) : 96 - 101
  • [8] A general copper-catalyzed synthesis of diaryl ethers
    Marcoux, JF
    Doye, S
    Buchwald, SL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) : 10539 - 10540
  • [9] Heterogeneous copper-catalyzed synthesis of diaryl sulfones
    Gong, Xinchi
    Shen, Zhengqi
    Wang, Ganghu
    Qu, Lingling
    Zhu, Chunyin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (48) : 10662 - 10668
  • [10] Copper-catalyzed synthesis of unsymmetrical diaryl chalcogenides from aryl iodides and diphenyl dichalcogenides
    Taniguchi, Nobukazu
    Onami, Tetsuo
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3259 - U3259