Reliable and Diverse Synthesis of Aryl Azides through Copper-Catalyzed Coupling of Boronic Acids or Esters with TMSN3

被引:80
|
作者
Li, Yu [1 ,2 ]
Gao, Lian-Xun [1 ]
Han, Fu-She [1 ]
机构
[1] Chinese Acad Sci, Changchun Inst Appl Chem, Changchun 130022, Jilin, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100864, Peoples R China
关键词
aryl azides; boronic acids; boronic esters; copper; cross-coupling; HUISGEN 1,3-DIPOLAR CYCLOADDITION; CLICK CHEMISTRY APPROACH; TETRAZOLE FORMATION; AROMATIC-AMINES; REACTIVITY; AZIRIDINES; CONVERSION; COMPLEXES; NITRILES; CYANIDES;
D O I
10.1002/chem.201000971
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Aryl azide formation: The copper-catalyzed coupling reaction of boronic esters and acids with TMSN3 have been presented as a highly efficient, simple, broadly applicable, and less hazardous methodology for the practi cal synthesis of aryl azides with structural diversity (see scheme). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:7969 / 7972
页数:4
相关论文
共 50 条
  • [1] Synthesis of Sulfoximines by Copper-Catalyzed Oxidative Coupling of Sulfinamides and Aryl Boronic Acids
    Zou, Xi
    Wang, Hanbing
    Gao, Bing
    ORGANIC LETTERS, 2023, : 7656 - 7660
  • [2] Copper-catalyzed synthesis of aryl azides and 1-aryl-1,2,3-triazoles from boronic acids
    Tao, Chuan-Zhou
    Cui, Xin
    Li, Juan
    Liu, Ai-Xiang
    Liu, Lei
    Guo, Qing-Xiang
    TETRAHEDRON LETTERS, 2007, 48 (20) : 3525 - 3529
  • [3] Synthesis of Hindered Anilines: Copper-Catalyzed Electrophilic Amination of Aryl Boronic Esters
    Rucker, Richard P.
    Whittaker, Aaron M.
    Dang, Hester
    Lalic, Gojko
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (16) : 3953 - 3956
  • [4] Facile synthesis of trifluoroethyl aryl ethers through copper-catalyzed coupling of CF3CH2OH with aryl- and heteroaryl boronic acids
    Wang, Ruixin
    Wang, Liang
    Zhang, Kena
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    TETRAHEDRON LETTERS, 2015, 56 (33) : 4815 - 4818
  • [5] Copper-catalyzed oxidative trifluoromethylation and trifluoromethylthiolation of aryl boronic acids
    Qing, Feng-Ling
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [6] Copper-catalyzed Chan-Lam coupling between sulfonyl azides and boronic acids at room temperature
    Moon, Soo-Yeon
    Kim, Won-Suk
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [7] Copper-Catalyzed Chan-Lam Coupling between Sulfonyl Azides and Boronic Acids at Room Temperature
    Moon, Soo-Yeon
    Nam, Jungsoo
    Rathwell, Kris
    Kim, Won-Suk
    ORGANIC LETTERS, 2014, 16 (02) : 338 - 341
  • [8] Copper-Catalyzed Synthesis of Activated Sulfonate Esters from Boronic Acids, DABSO, and Pentafluorophenol
    Vedovato, Vincent
    Talbot, Eric P. A.
    Willis, Michael C.
    ORGANIC LETTERS, 2018, 20 (17) : 5493 - 5496
  • [9] Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent
    Xu, Jun
    Luo, Dong-Fen
    Xiao, Bin
    Liu, Zhao-Jing
    Gong, Tian-Jun
    Fu, Yao
    Liu, Lei
    CHEMICAL COMMUNICATIONS, 2011, 47 (14) : 4300 - 4302
  • [10] Direct copper-catalyzed oxidative trifluoromethylthiolation of aryl boronic acids with AgSCF3
    Wu, Wei
    Wang, Biyun
    Ji, Xinfei
    Cao, Song
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1299 - 1303