Frozen aryldiazonium chlorides in radical reactions with alkenes and arenes

被引：5
|
作者：
Thon, Daniel [1 ]
Fuerst, Michael C. D. [1 ]
Altmann, Lisa-Marie [1 ]
Heinrich, Markus R. [1 ]
机构：
[1] Friedrich Alexander Univ Erlangen Nurnberg, Dept Chem & Pharm, Pharmaceut Chem, Nikolaus Fiebiger Str 10, D-91058 Erlangen, Germany
来源：
TETRAHEDRON | 2018年 / 74卷 / 38期
关键词：
Diazonium; Radical reaction; Carboamination; Carbohydroxylation; Biaryl; DIAZONIUM SALTS; ARYL DIAZONIUM; METAL-FREE; ARYLATION; CHEMISTRY; HETEROARENES; CATALYSIS; VERSATILE; ELECTRON; ANILINES;
D O I：
10.1016/j.tet.2018.05.089
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Frozen aryldiazonium chlorides have been investigated in radical alkene and arene functionalizations. Through freezing at - 84 degrees C, aryldiazonium chlorides, which otherwise show significant decomposition in aqueous solution after several hours at room temperature, can be stored for at least 20 days. In addition, the slow melting of aryldiazonium-containing ice cubes can serve as an alternative to syringe pumps that are commonly used if a controlled addition of the diazonium salt to the reaction mixture is required. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5289 / 5294
页数：6
相关论文
共 50 条
  • [1] FREE RADICAL ADDITION REACTIONS .4. REACTION OF METHANESULPHONYL AND METHANEDISULPHONYL CHLORIDES WITH ALKENES
    GOLDWHIT.H
    GIBSON, MS
    HARRIS, C
    TETRAHEDRON, 1965, 21 (10) : 2743 - &
  • [2] Base-Induced Radical Carboamination of Nonactivated Alkenes with Aryldiazonium Salts
    Kindt, Stephanie
    Wicht, Karina
    Heinrich, Markus R.
    ORGANIC LETTERS, 2015, 17 (24) : 6122 - 6125
  • [3] REDUCTION OF ARYLDIAZONIUM SALTS TO ARENES
    LAHOTI, RJ
    PARAMESWARAN, V
    WAGLE, DR
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1981, 20 (09): : 767 - 769
  • [4] RADICAL REACTION OF ETHYLENE SULFIDE WITH ARYLDIAZONIUM CHLORIDES IN PRESENCE OF CUCL2
    KOPYLOVA, BV
    YASHKINA, LV
    KARAPETYAN, SA
    FREIDLINA, RK
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1975, 24 (05): : 1090 - 1091
  • [5] 1,2-Diarylation of alkenes with aryldiazonium salts and arenes enabled by visible light photoredox catalysis
    Ouyang, Xuan-Hui
    Cheng, Jiang
    Li, Jin-Heng
    CHEMICAL COMMUNICATIONS, 2018, 54 (63) : 8745 - 8748
  • [6] Activation of aryl chlorides through π-coordination for radical coupling with arenes
    Nagata, Masaya
    Itonaga, Keita
    Mutoh, Yuichiro
    Endo, Kohei
    Ilies, Laurean
    CHEMISTRY LETTERS, 2024, 53 (12)
  • [7] TELOMERYZATION OF ACRYLONITRIL BY ARYLDIAZONIUM CHLORIDES
    FREIDLIN.RK
    KOPYLOVA, BV
    YASHKINA, LV
    DOKLADY AKADEMII NAUK SSSR, 1968, 183 (05): : 1113 - &
  • [8] Free radical reactions to generate alkenes and/or ionic reactions to generate hydroximoyl chlorides when β-nitrostyrenes react with triethylaluminium or diethylaluminium chloride
    Chu, CM
    Liu, JT
    Lin, WW
    Yao, CF
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (01): : 47 - 52
  • [9] FREE-RADICAL REACTIONS OF ARYLDIAZONIUM SALTS CATALYZED BY FERROCENE
    FREIDLINA, RK
    KANDROR, II
    GASANOV, RG
    KOPYLOVA, BV
    BRAGINA, IO
    YASHKINA, LV
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1984, 33 (04): : 758 - 761
  • [10] The tricarbonylchromium template for stereocontrol in radical reactions of arenes
    Merlic, CA
    Walsh, JC
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07): : 2265 - 2274
12345