Microwave-assisted organic synthesis: scale-up of palladium-catalyzed aminations using single-mode and multi-mode microwave equipment

被引：64
|
作者：
Loones, KTJ
Maes, BUW
Rombouts, G
Hostyn, S
Diels, G
机构：
[1] Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium
[2] Johnson & Johnson Pharmaceut Res & Dev, Janssen Pharmaceut, B-2340 Beerse, Belgium
来源：
TETRAHEDRON | 2005年 / 61卷 / 43期
关键词：
palladium; homogeneous catalysis; Buchwald-Hartwig amination; aryl chlorides; multi-mode cavity; single-mode cavity; microwave irradiation;
D O I：
10.1016/j.tet.2005.07.105
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Batch wise scale-up of Buchwald-Hartwig aminations under microwave irradiation has been investigated for the first time. Multi-mode (microSYNTH and MARS) (several vessels irradiated in parallel per batch) as well as single-mode (Discover) (one vessel irradiated per batch) platforms can be successfully used for this purpose with trifluoromethylbenzene (benzotrifluoride: BTF) as amination solvent. The obtained yields indicate a direct scalability in BTF for all the studied aminations. The Voyager equipment (based on a Discover platform) is the most convenient system since it allows an automatic continuous batch wise production without the necessity to manually load and unload reaction vessels. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：10338 / 10348
页数：11
相关论文
共 46 条
  • [31] Synthesis of polysubstituted imidazo[1,2-a]pyridines via microwave-assisted one-pot cyclization/Suzuki Coupling/Palladium-Catalyzed heteroarylation
    Koubachi, Jarnal
    El Kazzouli, Said
    Berteina-Raboin, Sabine
    Mouaddib, Abderrahim
    Guillaumet, Gerald
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (20): : 7650 - 7655
  • [32] Modular Synthesis of Biaryl-Substituted Phosphine Ligands: Application in Microwave-Assisted Palladium-Catalyzed C-N Cross-Coupling Reactions
    Singh, Chandani
    Rathod, Jayant
    Jha, Vishwajeet
    Panossian, Armen
    Kumar, Pradeep
    Leroux, Frederic R.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (29) : 6515 - 6525
  • [33] Microwave-assisted synthesis of functionalized carbazoles via palladium-catalyzed aryl C-H activation and study of their interactions with calf-thymus DNA
    Alam, Safiul
    Karim, Rejaul
    Khan, Aminur
    Mallick, Asifur Rahaman
    Sepay, Nayim
    Ghosh, Soumen
    SYNTHETIC COMMUNICATIONS, 2022, 52 (18) : 1834 - 1855
  • [34] Synthesis of core/shell Ti/TiOx photocatalyst via single-mode magnetic microwave assisted direct oxidation of TiH2
    Kato, Kunihiko
    Xin, Yunzi
    Hong, Jeongsoo
    Katsumata, Ken-ichi
    Shirai, Takashi
    ADVANCED POWDER TECHNOLOGY, 2020, 31 (05) : 1777 - 1783
  • [35] Microwave-assisted Synthesis of 5,6,7-Trisubstituted Pyrrolo[2,3-d]Pyrimidines via Palladium-catalyzed Heteroannulation with Internal Alkynes
    Park, Areum
    Choi, Sung Min
    Kim, Tae Sung
    Yum, Eul Kgun
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2019, 40 (11): : 1134 - 1137
  • [36] Using in situ Raman monitoring as a tool for rapid optimisation and scale-up of microwave-promoted organic synthesis:: esterification as an example
    Leadbeater, Nicholas E.
    Smith, Rebecca J.
    Barnard, T. Michael
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (05) : 822 - 825
  • [37] Controlled Heating of Palladium Dispersed Porous Alumina Tube and Continuous Oxidation of Ethylene Using Frequency-Variable Single-Mode Microwave Reactor
    Nishioka, Masateru
    Sato, Koichi
    Onodera, Ayumi
    Miyakawa, Masato
    Pacheco Tanaka, David A.
    Kasai, Makoto
    Miyazawa, Akira
    Suzuki, Toshishige M.
    INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2014, 53 (03) : 1073 - 1078
  • [38] Palladium-Catalyzed, Microwave-Assisted Synthesis of 3,4-Dihydro-3-oxo-2H-1,4-benzoxazines: An Improved Catalytic System and Multicomponent Process
    Feng, Gaofeng
    Wang, Shengnan
    Li, Weiting
    Chen, Fengjiang
    Qi, Chenze
    SYNTHESIS-STUTTGART, 2013, 45 (19): : 2711 - 2718
  • [39] Microwave-assisted palladium-catalyzed cross-coupling reactions between pyranoid glycals and aryl bromides. Synthesis of 2′-deoxy C-aryl-β-glycopyranosides
    Lei, Ming
    Gao, Liang
    Yang, Jin-Song
    TETRAHEDRON LETTERS, 2009, 50 (36) : 5135 - 5138
  • [40] Semi-continuous and fast synthesis of nanophase cubic BaTiO3 using a single-mode home-built microwave reactor
    Katsuki, Hiroaki
    Furuta, Sachiko
    Komarneni, Sridhar
    MATERIALS LETTERS, 2012, 83 : 8 - 10
12345