Hydroxy- and Aminophenyl Radicals from Arenediazonium Salts

被引:53
作者
Pratsch, Gerald [1 ]
Anger, Christian A. [2 ]
Ritter, Katharina [1 ]
Heinrich, Markus R. [1 ]
机构
[1] Univ Erlangen Nurnberg, Dept Chem Pharm, D-91052 Erlangen, Germany
[2] Tech Univ Munich, Dept Chem & Biochem, D-85747 Garching, Germany
关键词
allylation; arenediazonium salts; biaryls; C-C coupling; radical reactions; DIAZONIUM SALTS; ARYL; TETRAFLUOROBORATE; CONVENIENT; PHOTOLYSIS; REDUCTION; CHEMISTRY; ARYLATION; EFFICIENT; PYRIDINE;
D O I
10.1002/chem.201003713
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Arenediazonium salts are well-known sources of aryl radicals; however, the hydroxy- and amino-substituted derivatives 1, 2, and 3, which lead to the respective formation of radicals 4, 5, and 6, have rarely been employed in synthetic organic chemistry so far. New synthetic applications of these species have been found, and the properties that may have previously hindered their successful use have been investigated. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:4104 / 4108
页数:5
相关论文
共 64 条
  • [1] ARYLATIONS USING DIAZONIUM TETRAFLUOROBORATE AND PYRIDINE - A CONVENIENT SOURCE OF ARYL RADICALS
    ABRAMOVI.RA
    SAHA, JG
    [J]. TETRAHEDRON, 1965, 21 (12) : 3297 - &
  • [2] Synthesis and properties of photoactivatable phospholipid derivatives designed to probe the membrane-associate domains of proteins
    Alcaraz, ML
    Peng, L
    Klotz, P
    Goeldner, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) : 192 - 201
  • [3] Photochemical study of tris(benzotriazol-1-yl)methane
    Androsov, Dmitry A.
    Neckers, Douglas C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) : 1148 - 1152
  • [4] [Anonymous], 1884, Berichte Dtsch. Chem. Ges, DOI DOI 10.1002/CBER.18840170219
  • [5] LASER FLASH-PHOTOLYSIS STUDIES ON 4-OXOCYCLOHEXA-2,5-DIENYLIDENES
    ARNOLD, BR
    SCAIANO, JC
    BUCHER, GF
    SANDER, WW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (24) : 6469 - 6474
  • [6] Alkyl- and arylthiodediazoniations of dry arenediazonium o-benzenedisulfonimides.: Efficient and safe modifications of the Stadler and Ziegler reactions to prepare alkyl aryl and diaryl sulfides
    Barbero, M
    Degani, I
    Diulgheroff, N
    Dughera, S
    Fochi, R
    Migliaccio, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (18) : 5600 - 5608
  • [7] PHASE-TRANSFER-CATALYZED GOMBERG-BACHMANN SYNTHESIS OF UNSYMMETRICAL BIARENES - A SURVEY OF CATALYSTS AND SUBSTRATES
    BEADLE, JR
    KORZENIOWSKI, SH
    ROSENBERG, DE
    GARCIASLANGA, BJ
    GOKEL, GW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) : 1594 - 1603
  • [8] α1-Adrenoceptor agonists:: The identification of novel α1A subtype selective 2′-heteroaryl-2-(phenoxymethyl)imidazolines
    Bishop, MJ
    Barvian, KA
    Berman, J
    Bigham, EC
    Garrison, DT
    Gobel, MJ
    Hodson, SJ
    Irving, PE
    Liacos, JA
    Navas, F
    Saussy, DL
    Speake, JD
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (03) : 471 - 475
  • [9] Radical carbodiazenylation - A convenient and effective method to achieve carboamination of non-activated olefins
    Blank, Olga
    Wetzel, Alexander
    Ullrich, Daniela
    Heinrich, Markus R.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (18) : 3179 - 3189
  • [10] DIRECT OBSERVATION OF THE CYCLOPROPENE VINYLCARBENE REARRANGEMENT - MATRIX-ISOLATION OF BICYCLO[3.1.0]HEXA-3,5-DIEN-2-ONES
    BUCHER, G
    SANDER, W
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1346 - 1351