Suzuki cross-couplings of (hetero)aryl chlorides in the solid-state

被引：57
作者：
Cravotto, Giancarlo [1 ]
Garella, Davide [1 ]
Tagliapietra, Silvia [1 ]
Stolle, Achim [2 ]
Schuessler, Stefan [2 ]
Leonhardt, Silke E. S. [2 ]
Ondruschka, Bernd [2 ]
机构：
[1] Univ Turin, Dipartimento Sci & Tecnol Farm, I-10125 Turin, Italy
[2] Univ Jena, Inst Tech Chem & Environm Chem ITUC, D-07743 Jena, Germany
来源：
NEW JOURNAL OF CHEMISTRY | 2012年 / 36卷 / 06期
关键词：
HIGH-INTENSITY ULTRASOUND; HECK REACTION; ORGANIC-SYNTHESIS; BALL MILL; CHITOSAN; COMPLEX;
D O I：
10.1039/c2nj40064b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The ultrasound-assisted cross-linking of chitosan with hexamethylene diisocyanate with the simultaneous incorporation of Pd(OAc)(2) resulted in a catalyst which is suitable for the solid-state Suzuki cross-coupling of poorly reactive (hetero)aryl chlorides with phenylboronic acid. Reactions were carried out solvent-free in a planetary ball mill allowing the catalyst to be recycled several times.
引用
收藏
页码：1304 / 1307
页数：4
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共 23 条
  • [1] Solvent-free and time-efficient Suzuki-Miyaura reaction in a ball mill: the solid reagent system KF-Al2O3 under inspection
    Bernhardt, Franziska
    Trotzki, Ronald
    Szuppa, Tony
    Stolle, Achim
    Ondruschka, Bernd
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6
  • [2] High-intensity ultrasound and microwave, alone or combined, promote Pd/C-catalyzed aryl-aryl couplings
    Cravotto, G
    Beggiato, M
    Penoni, A
    Palmisano, G
    Tollari, S
    Lévêque, JM
    Bonrath, W
    [J]. TETRAHEDRON LETTERS, 2005, 46 (13) : 2267 - 2271
  • [3] Chemical modification of chitosan under high-intensity ultrasound
    Cravotto, G
    Tagliapietra, S
    Robaldo, B
    Trotta, M
    [J]. ULTRASONICS SONOCHEMISTRY, 2005, 12 (1-2) : 95 - 98
  • [4] Solvent-free Sonogashira coupling reaction via high speed ball milling
    Fulmer, Dennis A.
    Shearouse, William C.
    Medonza, Shareika T.
    Mack, James
    [J]. GREEN CHEMISTRY, 2009, 11 (11) : 1821 - 1825
  • [5] Mechanochemistry: opportunities for new and cleaner synthesis
    James, Stuart L.
    Adams, Christopher J.
    Bolm, Carsten
    Braga, Dario
    Collier, Paul
    Friscic, Tomislav
    Grepioni, Fabrizia
    Harris, Kenneth D. M.
    Hyett, Geoff
    Jones, William
    Krebs, Anke
    Mack, James
    Maini, Lucia
    Orpen, A. Guy
    Parkin, Ivan P.
    Shearouse, William C.
    Steed, Jonathan W.
    Waddell, Daniel C.
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) : 413 - 447
  • [6] Waste-free synthesis and production all across chemistry with the benefit of self-assembled crystal packings
    Kaupp, Gerd
    [J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2008, 21 (7-8) : 630 - 643
  • [7] Ligand-free palladium catalysis of aryl coupling reactions facilitated by grinding
    Klingensmith, LM
    Leadbeater, NE
    [J]. TETRAHEDRON LETTERS, 2003, 44 (04) : 765 - 768
  • [8] Chitosan as a support for heterogeneous Pd catalysts in liquid phase catalysis
    Leonhardt, Silke E. S.
    Stolle, Achim
    Ondruschka, Bernd
    Cravotto, Giancarlo
    De Leo, Cristina
    Jandt, Klaus D.
    Keller, Thomas F.
    [J]. APPLIED CATALYSIS A-GENERAL, 2010, 379 (1-2) : 30 - 37
  • [9] In situ cross-linked chitosan Cu(I) or Pd(II) complexes as a versatile, eco-friendly recyclable solid catalyst
    Martina, Katia
    Leonhardt, Silke E. S.
    Ondruschka, Bernd
    Curini, Massimo
    Binello, Arianna
    Cravotto, Giancarlo
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 334 (1-2) : 60 - 64
  • [10] The Suzuki reaction under solvent-free conditions
    Nielsen, SF
    Peters, D
    Axelsson, O
    [J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (19) : 3501 - 3509
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