A General Rhodium-Catalyzed Cyanation of Aryl and Alkenyl Boronic Acids

被引:203
作者
Anbarasan, Pazhamalai [1 ]
Neumann, Helfried [1 ]
Beller, Matthias [1 ]
机构
[1] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
benzonitriles; boronic acids; cyanation; homogeneous catalysis; rhodium; ARYLBORONIC ACIDS; PALLADIUM(II)-CATALYZED ADDITION; POTASSIUM HEXACYANOFERRATE(II); CONVENIENT PROCEDURE; EFFICIENT SYNTHESIS; BROMIDES; HALIDES; ALKYNES; SYSTEM; KETONES;
D O I
10.1002/anie.201006044
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Give me a cyanide: N-cyano-N-phenyl-p-methylbenzenesulfonamide as a cyanation reagent allows the synthesis of aryl(alkenyl) nitriles in good yield under mild conditions (see scheme; cod=cycloocta-1,5-diene). Combination of the procedure with the direct borylation of arenes and hydroboration of alkynes leads to the straightforward synthesis of various nitriles. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:519 / 522
页数:4
相关论文
共 87 条
  • [51] Improving palladium-catalyzed cyanation of aryl halides: development of a state-of-the-art methodology using potassium hexacyanoferrate(II) as cyanating agent
    Schareina, T
    Zapf, A
    Beller, M
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) : 4576 - 4583
  • [52] Potassium hexacyanoferrate(II) - a new cyanating agent for the palladium-catalyzed cyanation of aryl halides
    Schareina, T
    Zapf, A
    Beller, M
    [J]. CHEMICAL COMMUNICATIONS, 2004, (12) : 1388 - 1389
  • [53] A Bio-inspired Copper Catalyst System for Practical Catalytic Cyanation of Aryl Bromides
    Schareina, Thomas
    Zapf, Alexander
    Cotte, Alain
    Mueller, Nikolaus
    Beller, Matthias
    [J]. SYNTHESIS-STUTTGART, 2008, 20 (20): : 3351 - 3355
  • [54] A state-of-the-art cyanation of aryl bromides:: A novel and versatile copper catalyst system inspired by nature
    Schareina, Thomas
    Zapf, Alexander
    Maegerlein, Wolfgang
    Mueller, Nikolaus
    Beller, Matthias
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (21) : 6249 - 6254
  • [55] Copper-catalyzed cyanation of heteroaryl bromides:: A novel and versatile catalyst system inspired by nature
    Schareina, Thomas
    Zapf, Alexander
    Maegerlein, Wolfgang
    Mueller, Nikolaus
    Beller, Matthias
    [J]. SYNLETT, 2007, (04) : 555 - 558
  • [56] A new palladium catalyst system for the cyanation of aryl chlorides with K4[Fe(CN)6]
    Schareina, Thomas
    Zapf, Alexander
    Maegerlein, Wolfgang
    Mueller, Nikolaus
    Beller, Matthias
    [J]. TETRAHEDRON LETTERS, 2007, 48 (07) : 1087 - 1090
  • [57] Increasing the Scope of Palladium-Catalyzed Cyanations of Aryl Chlorides
    Schareina, Thomas
    Jackstell, Ralf
    Schulz, Thomas
    Zapf, Alexander
    Cotte, Alain
    Gotta, Matthias
    Beller, Matthias
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (04) : 643 - 648
  • [58] Synthesis of α-keto esters by the rhodium-catalysed reaction of cyanoformate with arylboronic acids
    Shimizu, Hiroshi
    Murakami, Masahiro
    [J]. CHEMICAL COMMUNICATIONS, 2007, (27) : 2855 - 2857
  • [59] A New Route to Acyclic Diaminocarbenes via Lithium-Halogen Exchange
    Snead, David R.
    Ghiviriga, Ion
    Abboud, Khalil A.
    Hong, Sukwon
    [J]. ORGANIC LETTERS, 2009, 11 (15) : 3274 - 3277
  • [60] STADTMULLER H, 1995, SYNTHESIS-STUTTGART, P69