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
  • [21] Synthesis of Highly Functionalized Diaryl Ketones by Palladium-Catalyzed Carbonylative Cross-Coupling Reaction Between Triarylbismuthines and Aryl(Heteroaryl) Iodides
    Dansereau, Julien
    Gautreau, Stephane
    Gagnon, Alexandre
    CHEMISTRYSELECT, 2017, 2 (08): : 2593 - 2599
  • [22] Nickel-catalyzed Kumada Cross-coupling Reaction for the Synthesis of 2,4-Diarylquinazolines
    Ye, Xinglin
    Yuan, Zhihan
    Zhou, Yirong
    Yang, Qin
    Xie, Yepeng
    Deng, Zhihong
    Peng, Yiyuan
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (06) : 1956 - 1962
  • [23] Iodine-Promoted Synthesis of 4-Aryl-2-(arylsulfonyl)quinolones by Desulfurative C-S Cross-Coupling Reaction of Quinoline-2-thiones with Sodium Sulfinates
    Yang, Guo-Chao
    Wang, Xi-Chun
    Quan, Zheng-Jun
    SYNLETT, 2020, 31 (15) : 1527 - 1531
  • [24] Oxidative Dehydrosulfurative Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Alkynes for Access to 2-Alkynylpyrimidines
    Pham, Ngoc Son Le
    Shin, Hyunik
    Kang, Jun Yong
    Sohn, Jeong-Hun
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (07): : 5087 - 5096
  • [25] Cu(OAc)2 catalyzed Sonogashira cross-coupling reaction in amines
    Guo, Sheng Mei
    Deng, Chen Liang
    Li, Jin Heng
    CHINESE CHEMICAL LETTERS, 2007, 18 (01) : 13 - 16
  • [26] Cu(OAc)2 catalyzed Sonogashira cross-coupling reaction in amines
    Sheng Mei Guo Chen Liang Deng Jin Heng Li~* Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research(Ministry of Education)
    Chinese Chemical Letters, 2007, (01) : 13 - 16
  • [27] Synthesis of quinoxalines and pyrido[2,3-b]pyrazines by Suzuki–Miyaura cross-coupling reaction
    Arjun Kumbhar
    Sanjay Jadhav
    Rajashri Salunkhe
    Research on Chemical Intermediates, 2016, 42 : 5431 - 5440
  • [28] Stereoselective synthesis of (Z,E)-2-phenylselenobutadienes by palladium-catalyzed cross-coupling reaction
    Cai, MZ
    Huang, JD
    Peng, CY
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 681 (1-2) : 98 - 101
  • [29] Transition metal-free Suzuki type cross-coupling reaction for the synthesis of dissymmetric ketones
    Jadhav, Sanjay
    Rashinkar, Gajanan
    Salunkhe, Rajashri
    Kumbhar, Arjun
    TETRAHEDRON LETTERS, 2017, 58 (33) : 3201 - 3204
  • [30] Synthesis of 2,2′-Bipyridines via Suzuki-Miyaura Cross-Coupling
    Guetz, Christoph
    Luetzen, Arne
    SYNTHESIS-STUTTGART, 2010, (01): : 85 - 90
12345