Utility of a heterogeneous palladium catalyst for the synthesis of a molecular semiconductor via Stille, Suzuki, and direct heteroarylation cross-coupling reactions

作者: Seth M. McAfee , Jenny S. J. McCahill , Casper M. Macaulay , Arthur D. Hendsbee , Gregory C. Welch

DOI: 10.1039/C5RA02468D

关键词: Suzuki reactionCombinatorial chemistrySelectivityHeterogeneous catalysisStille reactionPhotochemistryArylMolecular semiconductorCatalysisChemistryCoupling reaction

摘要: Demonstration of the utility of a commercially available heterogeneous palladium catalyst in the synthesis of a relevant high performance molecular semiconductor.

参考文章(57)
Giuseppe Marzano, Cosimo V. Ciasca, Francesco Babudri, Gabriele Bianchi, Andrea Pellegrino, Riccardo Po, Gianluca M. Farinola, Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production European Journal of Organic Chemistry. ,vol. 2014, pp. 6583- 6614 ,(2014) , 10.1002/EJOC.201402226
Frederik C. Krebs, René B. Nyberg, Mikkel Jørgensen, Influence of Residual Catalyst on the Properties of Conjugated Polyphenylenevinylene Materials: Palladium Nanoparticles and Poor Electrical Performance Chemistry of Materials. ,vol. 16, pp. 1313- 1318 ,(2004) , 10.1021/CM035205W
Tommie W. Kelley, Paul F. Baude, Chris Gerlach, David E. Ender, Dawn Muyres, Michael A. Haase, Dennis E. Vogel, Steven D. Theiss, Recent Progress in Organic Electronics: Materials, Devices, and Processes Chemistry of Materials. ,vol. 16, pp. 4413- 4422 ,(2004) , 10.1021/CM049614J
Hong-Hai Zhang, Chun-Hui Xing, Qiao-Sheng Hu, Controlled Pd(0)/t-Bu3P-catalyzed Suzuki cross-coupling polymerization of AB-type monomers with PhPd(t-Bu3P)I or Pd2(dba)3/t-Bu3P/ArI as the initiator. Journal of the American Chemical Society. ,vol. 134, pp. 13156- 13159 ,(2012) , 10.1021/JA302745T
Xuecheng Chen, Yuqing Hou, Hang Wang, Yang Cao, Junhui He, Facile Deposition of Pd Nanoparticles on Carbon Nanotube Microparticles and Their Catalytic Activity for Suzuki Coupling Reactions Journal of Physical Chemistry C. ,vol. 112, pp. 8172- 8176 ,(2008) , 10.1021/JP800610Q
Arif Daştan, Aditya Kulkarni, Béla Török, None, Environmentally benign synthesis of heterocyclic compounds by combined microwave-assisted heterogeneous catalytic approaches† Green Chemistry. ,vol. 14, pp. 17- 37 ,(2012) , 10.1039/C1GC15837F
Daniel J. Burke, Darren J. Lipomi, Green chemistry for organic solar cells Energy and Environmental Science. ,vol. 6, pp. 2053- 2066 ,(2013) , 10.1039/C3EE41096J
Vivek Polshettiwar, Christophe Len, Aziz Fihri, Silica-supported palladium: Sustainable catalysts for cross-coupling reactions Coordination Chemistry Reviews. ,vol. 253, pp. 2599- 2626 ,(2009) , 10.1016/J.CCR.2009.06.001
Mathieu Lemay, Valerica Pandarus, Mathieu Simard, Olivier Marion, Lynda Tremblay, François Béland, SiliaCat ® S-Pd and SiliaCat DPP-Pd: Highly Reactive and Reusable Heterogeneous Silica-Based Palladium Catalysts Topics in Catalysis. ,vol. 53, pp. 1059- 1062 ,(2010) , 10.1007/S11244-010-9532-6