Transition-metal-free synthesis of arylboronates via thermal generation of aryl radicals from triarylbismuthines in air

被引:0
|
作者
Yamamoto, Yuki [1 ]
Konakazawa, Yuki [1 ]
Fujiwara, Kohsuke [2 ]
Ogawa, Akiya [3 ]
机构
[1] Univ Yamanashi, Grad Fac Interdisciplinary Res, 4-4-37 Takeda, Kofu, Yamanashi 4008510, Japan
[2] Osaka Metropolitan Univ, Grad Sch Engn, Dept Appl Chem, 1-1 Gakuen Cho,Nakaku, Sakai, Osaka 5998531, Japan
[3] Osaka Metropolitan Univ, Org Res Promot, 1-1 Gakuen Cho,Nakaku, Sakai, Osaka 5998531, Japan
来源
基金
日本学术振兴会;
关键词
arylboronates; bis(pinacolato)diboron; radical reactions; transition-metal-free synthesis; triarylbismuthines; CROSS-COUPLING REACTION; CATALYZED BORYLATION; AROMATIC KETONES; ARYLATION; ACTIVATION; ROUTE; FUNCTIONALIZATION; TRIPHENYLBISMUTH; ARYLHYDRAZINES; DIALKOXYBORANE;
D O I
10.3762/bjoc.20.216
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and versatile synthesis of arylboronates has been achieved by using triarylbismuthines as aryl radical sources under transition-metal-free and open-air conditions. Conventional methods required photoirradiation or electrolysis to generate aryl radicals from triarylbismuthines. In this study, it was found that simply heating the solution of triarylbismuthines in benzotrifluoride (BTF) in air successfully led to the generation of aryl radicals, and the subsequent reaction with bis(pinacolato)diboron afforded a variety of arylboronates in moderate to good yields.
引用
收藏
页码:2577 / 2584
页数:8
相关论文
共 50 条
  • [31] Transition-metal-free α-arylation of nitroketones with diaryliodonium salts for the synthesis of tertiary α-aryl, α-nitro ketones
    An, Yang
    Zhang, Xiao-Ming
    Li, Ze-Yu
    Xiong, Wen-Hui
    Yu, Run-Dong
    Zhang, Fu-Min
    CHEMICAL COMMUNICATIONS, 2019, 55 (01) : 119 - 122
  • [32] Generation of α-Boryl Radicals and Their Conjugate Addition to Enones: Transition-Metal-Free Alkylation of gem-Diborylalkanes
    Wu, Chaoqiang
    Bao, Zhicheng
    Dou, Bowen
    Wang, Jianbo
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (07) : 2294 - 2298
  • [33] Transition-Metal-Free Indirect Friedlander Synthesis of Quinolines from Alcohols
    Martinez, Ricardo
    Ramon, Diego J.
    Yus, Miguel
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (24): : 9778 - 9780
  • [34] Direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions
    Xiong, Biquan
    Wang, Gang
    Xiong, Tao
    Wan, Liming
    Zhou, Congshan
    Liu, Yu
    Zhang, Panliang
    Yang, Changan
    Tang, Kewen
    TETRAHEDRON LETTERS, 2018, 59 (32) : 3139 - 3142
  • [35] Synthesis of β-Hydroxy Aryl Selenides via Transition-Metal-Free Three-Component Reaction of Arylamines, Elemental Selenium, and Epoxides
    Wang, Hongwei
    Li, Hongchen
    Bai, Yalong
    Hei, Yanling
    Chen, Junwei
    Yu, Guoqi
    Zhou, Yun-Bing
    SYNTHESIS-STUTTGART, 2021, 53 (19): : 3621 - 3629
  • [36] Scalable Transition-Metal-Free Synthesis of Aryl Amines from Aryl Chlorides through X@RONa-Catalyzed Benzyne Formation
    Yao, Jia-Lin
    Zhang, Zining
    Li, Zhi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (13) : 8839 - 8846
  • [37] Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes
    He, Qing
    Wang, Liwen
    Liang, Yong
    Zhang, Zunting
    Wnuk, Stanislaw F.
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19): : 9422 - 9427
  • [38] Aqueous Synthesis of 1-H-2-Substituted Benzimidazoles via Transition-Metal-Free Intramolecular Amination of Aryl Iodides
    Chen, Chunxia
    Chen, Chen
    Li, Bin
    Tao, Jingwei
    Peng, Jinsong
    MOLECULES, 2012, 17 (11): : 12506 - 12520
  • [39] Transition-metal-free decarboxylative ipso amination of aryl carboxylic acids
    Zhang, Jing
    Hou, Ye-Xing
    Tang, Yan-Liu
    Xu, Ji-Hang
    Liu, Zi-Kui
    Gao, Yang
    Hu, Xiao-Qiang
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (13) : 3434 - 3439
  • [40] Transition-Metal-Free Oxyarylation of Alkenes with Aryl Diazonium Salts and TEMPONa
    Hartmann, Marcel
    Li, Yi
    Studer, Armido
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (40) : 16516 - 16519