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
  • [41] Transition-Metal-Free Synthesis of 4-Alkynylquinazolines
    Ucar, Sefa
    Dastan, Arif
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (13)
  • [42] Transition-metal-free synthesis of β-trifluoromethylated enamines with trifluoromethanesulfinate
    Jiang, Huanfeng
    Huang, Wei
    Yu, Yue
    Yi, Songjian
    Li, Jiawei
    Wu, Wanqing
    CHEMICAL COMMUNICATIONS, 2017, 53 (54) : 7473 - 7476
  • [43] Transition-Metal-Free ipso-Trifluoromethyithiolation of Lithium Aryl Boronates
    Shen, Feng
    Zheng, Hanliang
    Xue, Xiao-Song
    Lu, Long
    Shen, Qilong
    ORGANIC LETTERS, 2019, 21 (16) : 6347 - 6351
  • [44] Recent Advances in the Transition-Metal-Free Synthesis of Quinazolines
    Tamatam, Rekha
    Shin, Dongyun
    MOLECULES, 2023, 28 (07):
  • [45] Recent advances in the transition-metal-free synthesis of quinoxalines
    Borah, Biplob
    Chowhan, L. Raju
    RSC ADVANCES, 2021, 11 (59) : 37325 - 37353
  • [46] Transition-Metal-Free Synthesis of Pyridine Derivatives by Thermal Cyclization of N -Propargyl Enamines
    Chikayuki, Yuya
    Miyashige, Takakane
    Yonekawa, Shiori
    Kirita, Akiko
    Matsuo, Natsuko
    Teramoto, Hiroyoshi
    Sasaki, Shigeru
    Higashiyama, Kimio
    Yamauchi, Takayasu
    SYNTHESIS-STUTTGART, 2020, 52 (07): : 1113 - 1121
  • [47] Transition-metal-free oxidative intermolecular cyclization reaction: synthesis of 2-aryl-4-quinolones
    Ma, Haojie
    Guo, Cui
    Zhan, Zhenzhen
    Lu, Guoqiang
    Zhang, Yixin
    Luo, Xinliang
    Cui, XinFeng
    Huang, Guosheng
    NEW JOURNAL OF CHEMISTRY, 2017, 41 (13) : 5280 - 5283
  • [48] Synthesis of Dibenzosultams by "Transition-Metal-Free" Photoinduced Intramolecular Arylation of N-Aryl-2-halobenzenesulfonamides
    Guerra, Walter D.
    Rossi, Roberto A.
    Pierini, Adriana B.
    Barolo, Silvia M.
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (12): : 4965 - 4973
  • [49] Transition-metal-free synthesis of poly(phenylene ethynylene)s with alternating aryl-perfluoroaryl units
    Dutta, Tanmoy
    Woody, Kathy B.
    Watson, Mark D.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (02) : 452 - +
  • [50] Transition-metal-free regioselective synthesis of alkylboronates from arylacetylenes and vinyl arenes
    Yang, Kai
    Song, Qiuling
    GREEN CHEMISTRY, 2016, 18 (04) : 932 - 936