Liebeskind-Srogl-type cross-coupling reaction of azole-2-thiones with triarylbismuthines: Synthesis of 2-arylazoles

被引：4
|
作者：
Murata, Yuki [1 ]
Terazoe, Aki [1 ]
Kiba, Misato [1 ]
Kitamura, Yuki [1 ]
Matsumura, Mio [1 ]
Yasuike, Shuji [1 ]
机构：
[1] Aichi Gakuin Univ, Sch Pharmaceut Sci, Chikusa Ku, 1-100 Kusumoto Cho, Nagoya, Aichi 4648650, Japan
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 30期
关键词：
Bismuth; Cross-coupling reaction; Palladium catalyst; Thiazole; Triarylbismuthine; CARBON-CARBON; BORONIC ACIDS; CYCLIC THIOAMIDES; BOND FORMATION; PALLADIUM; REAGENTS; ARYLATION;
D O I：
10.1016/j.tetlet.2020.152152
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Liebeskind-Srogl-type C(HetAr)-C(Ar) bond formation using trivalent organobismuth compounds as a new class of arylating reagents is described. The reaction of benzazole-2-thiones with triarylbismuthines in the presence of 10 mol% Pd(dba)(2) and 2.0 equiv. Cu(OAc)(2) at 80 degrees C affords 2-arylbenzothiazoles, benzoxazoles, and N-methyl benzimidazole in moderate-to-high yield. The reaction is sensitive to the electronic nature of triarylbismuthines: compounds bearing an electron-withdrawing group on the phenyl ring showed higher reactivity than those having an electron-donating group. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数：4
相关论文
共 50 条
  • [41] Synthesis of 2-Aryl-4H-thiochromen-4-one Derivatives via a Cross-Coupling Reaction
    Li, Peng
    Li, Shengnan
    Li, Gang
    Huang, Haihong
    ACS OMEGA, 2021, 6 (22): : 14655 - 14663
  • [42] Synthesis of 2,4,6-trisubstituted pyridines using palladium-catalyzed cross-coupling reaction
    Trejo, Pedro
    Hernandez Campos, Alicia
    Castillo-Bocanegra, Rafael
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [43] Synthesis of 2-Arylpyrazolo[1,5-a]pyridines by Suzuki-Miyaura Cross-Coupling Reaction
    Umei, Kentaro
    Nishigaya, Yosuke
    Kamiya, Megumi
    Kohno, Yasushi
    Seto, Shigeki
    SYNTHESIS-STUTTGART, 2015, 47 (20): : 3221 - 3230
  • [44] Synthesis of 3-alkyl-6-methyl-1,2,4,5-tetrazines via a Sonogashira-type cross-coupling reaction
    Ros, Enric
    Prades, Amparo
    Forson, Dominique
    Smyth, Jacqueline
    Verdaguer, Xavier
    Ribas de Pouplana, Lluis
    Riera, Antoni
    CHEMICAL COMMUNICATIONS, 2020, 56 (75) : 11086 - 11089
  • [45] Synthesis and application of SBA-Pr-Py@Pd in Suzuki-type cross-coupling reaction
    Mohammadi Ziarani, Ghodsi
    Ebrahimi, Zahra
    Mohajer, Fatemeh
    Badiei, Alireza
    RESEARCH ON CHEMICAL INTERMEDIATES, 2021, 47 (11) : 4583 - 4594
  • [46] Synthesis and application of SBA-Pr-Py@Pd in Suzuki-type cross-coupling reaction
    Ghodsi Mohammadi Ziarani
    Zahra Ebrahimi
    Fatemeh Mohajer
    Alireza Badiei
    Research on Chemical Intermediates, 2021, 47 : 4583 - 4594
  • [47] Stereoselective Synthesis of ( Z )-2-Bromo-2-CF 3 -Vinyl Phenyl Sulfide and its Sonogashira Cross-Coupling Reaction
    Fukuda, Yui
    Kikumura, Takumi
    Sakoda, Saki
    Ikeda, Genki
    Nakamura, Yuki
    Dojyo, Masakazu
    Yamada, Yasunori
    Hanamoto, Takeshi
    SYNLETT, 2019, 30 (07) : 837 - 840
  • [48] Synthesis of Soai Type 2-Arylpyrimidine-5-carbaldehydes through Desulfurative Cross-Coupling with Arylboronic Acids
    Maltsev, Oleg V.
    Rausch, Rodger
    Quan, Zheng-Jun
    Hintermann, Lukas
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (33) : 7426 - 7432
  • [49] Supported synthesis and functionnalization of 2′-deoxyuridine by Suzuki-Miyaura cross-coupling
    El Kazzouli, Said
    Berteina-Raboin, Sabine
    Agrofoglio, Luigi A.
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2007, 26 (10-12): : 1395 - 1398
  • [50] An Efficient Method for the Synthesis of 2-Methylallyl Alkenes by Cross-Coupling Reactions
    Tabele, Clemence
    Curti, Christophe
    Primas, Nicolas
    Kabri, Youssef
    Remusat, Vincent
    Vanelle, Patrice
    SYNTHESIS-STUTTGART, 2015, 47 (21): : 3339 - 3346
12345