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Pure Appl. Chem., 2001, Vol. 73, No. 1, pp. 119-128

http://dx.doi.org/10.1351/pac200173010119

Rapid screening and combinatorial methods in homogeneous organometallic catalysis

Jennifer A. Loch and Robert H. Crabtree

Department of Chemistry, Yale University, P.O. Box 208107, New Haven, CT 06520-8107, USA

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  • Bakherad Mohammad, Jajarmi Saeideh: A dithizone-functionalized polystyrene resin-supported Pd(II) complex as an effective catalyst for Suzuki, Heck, and copper-free Sonogashira reactions under aerobic conditions in water. Journal of Molecular Catalysis A: Chemical 2013, 370, 152. <http://dx.doi.org/10.1016/j.molcata.2013.01.009>
  • Xiao Ruian, Zhao Hong, Cai Mingzhong: MCM-41-immobilized bidentate nitrogen copper(I) complex: a highly efficient and recyclable catalyst for Buchwald N-arylation of indoles. Tetrahedron 2013, 69, 5444. <http://dx.doi.org/10.1016/j.tet.2013.04.106>
  • Vannucci A. K., Alibabaei L., Losego M. D., Concepcion J. J., Kalanyan B., Parsons G. N., Meyer T. J.: Crossing the divide between homogeneous and heterogeneous catalysis in water oxidation. Proceedings of the National Academy of Sciences 2013, 110, 20918. <http://dx.doi.org/10.1073/pnas.1319832110>
  • Magna L., Harry S., Faraj A., Olivier-Bourbigou H.: Cobalt Hydroformylation of Olefins in a Biphasic System Using Ionic Liquids – Development and Reaction Optimization by a Design Experiment Approach. Oil Gas Sci. Technol. – Rev. IFP Energies nouvelles 2013, 68, 415. <http://dx.doi.org/10.2516/ogst/2013131>
  • Iranpoor Nasser, Firouzabadi Habib, Safavi Afsaneh, Motevalli Somayeh, Doroodmand Mohammad M.: Palladium nanoparticles supported on SiO2 by chemical vapor deposition (CVD) technique as efficient catalyst for Suzuki-Miyaura coupling of aryl bromides and iodides: selective coupling of halophenols. Appl. Organometal. Chem. 2012, 26, 417. <http://dx.doi.org/10.1002/aoc.2868>
  • Xiao Ruian, Hao Wenyan, Ai Jinting, Cai Ming-Zhong: A practical synthesis of 2-aminobenzothiazoles via the tandem reactions of 2-haloanilines with isothiocyanates catalyzed by immobilization of copper in MCM-41. Journal of Organometallic Chemistry 2012, 705, 44. <http://dx.doi.org/10.1016/j.jorganchem.2012.01.014>
  • Leung Diana, Kang Sung Ok, Anslyn Eric V.: Rapid determination of enantiomeric excess: a focus on optical approaches. Chemical Society Review 2012, 41, 448. <http://dx.doi.org/10.1039/c1cs15135e>
  • Friest Jacob A., Broussy Sylvain, Chung Woo Jin, Berkowitz David B.: Combinatorial Catalysis Employing a Visible Enzymatic Beacon in Real Time: Synthetically Versatile (Pseudo)Halometalation/Carbocyclizations. angew chemie 2011, 123, 9057. <http://dx.doi.org/10.1002/ange.201103365>
  • Friest Jacob A., Broussy Sylvain, Chung Woo Jin, Berkowitz David B.: Combinatorial Catalysis Employing a Visible Enzymatic Beacon in Real Time: Synthetically Versatile (Pseudo)Halometalation/Carbocyclizations. Angew Chem Int E 2011, 50, 8895. <http://dx.doi.org/10.1002/anie.201103365>
  • Zhao Hong, Ding Guodong, Xu Li, Cai Mingzhong: A phosphine-free heterogeneous Suzuki-Miyaura reaction of aryl bromides catalyzed by MCM-41-supported tridentate nitrogen palladium complex under air : A phosphine-free heterogeneous Suzuki-Miyaura reaction. Appl Organometal Chem 2011, 25, 871. <http://dx.doi.org/10.1002/aoc.1854>
  • Corthals Steven, Witvrouwen Toon, Jacobs Pierre, Sels Bert: Development of dry reforming catalysts at elevated pressure: D-optimal vs. full factorial design. Catal Today 2011, 159, 12. <http://dx.doi.org/10.1016/j.cattod.2010.06.021>
  • Zhao Hong, Peng Jian, Xiao Ruian, Cai Mingzhong: A simple, efficient and recyclable phosphine-free catalytic system for Suzuki–Miyaura reaction of aryl bromides. Journal of Molecular Catalysis A 2011, 337, 56. <http://dx.doi.org/10.1016/j.molcata.2011.01.014>
  • Kang Sung Ok, Lynch Vincent M., Day Victor W., Anslyn Eric V.: Enthalpy- vs Entropy-Driven Complexation of Homoallylic Alcohols by Rhodium(I) Complexes. Organomettalics 2011, 30, 6233. <http://dx.doi.org/10.1021/om200793p>
  • Loch Jennifer A., Crabtree Robert H.: ChemInform Abstract: Rapid Screening and Combinatorial Methods in Homogeneous Organometallic Catalysis. ChemInform 2010, 32, no. <http://dx.doi.org/10.1002/chin.200138271>
  • Bhunia Susmita, Sen Rupam, Koner Subratanath: Anchoring of palladium(II) in chemically modified mesoporous silica: An efficient heterogeneous catalyst for Suzuki cross-coupling reaction. Inorg Chim Ada 2010, 363, 3993. <http://dx.doi.org/10.1016/j.ica.2010.07.076>
  • Yılmaz Filiz, Mutlu Aylin, Ünver Hakan, Kurtça Mehmet, Kani İbrahim: Hydrogenation of olefins catalyzed by Pd(II) complexes containing a perfluoroalkylated S,O-chelating ligand in supercritical CO2 and organic solvents. J Sup Fluids 2010, 54, 202. <http://dx.doi.org/10.1016/j.supflu.2010.04.014>
  • ZHENG Guomin, WANG Pingping, CAI Mingzhong: A New Route to Biaryl Ketones via Carbonylative Suzuki Coupling Catalyzed by MCM-41-supported Bidentate Phosphine Palladium(0) Complex. Chin J Chem 2009, 27, 1420. <http://dx.doi.org/10.1002/cjoc.200990239>
  • Bakherad Mohammad, Bahramian Bahram, Nasr-Isfahani Hossein, Keivanloo Ali, Doostmohammadi Nesa: Polystyrene-supported palladium(II) ethylenediamine complex: A highly active and recyclable catalyst for the synthesis of 2-benzylimidazo[2,1-b]pyridines through heteroannulation of acetylenic compounds. J Heterocyclic Chem 2009, 46, 100. <http://dx.doi.org/10.1002/jhet.16>
  • Hao Wenyan, Sha Junchao, Sheng Shouri, Cai Mingzhong: The first heterogeneous carbonylative Sonogashira coupling reaction catalyzed by MCM-41-supported bidentate phosphine palladium(0) complex. Journal of Molecular Catalysis A 2009, 298, 94. <http://dx.doi.org/10.1016/j.molcata.2008.09.031>
  • Jana Sreyashi, Haldar Satyajit, Koner Subratanath: Heterogeneous Suzuki and Stille coupling reactions using highly efficient palladium(0) immobilized MCM-41 catalyst. Tetrahetron Lett 2009, 50, 4820. <http://dx.doi.org/10.1016/j.tetlet.2009.05.098>
  • Zhao Hong, Wang Yue, Sha Junchao, Sheng Shouri, Cai Mingzhong: MCM-41-supported bidentate phosphine palladium(0) complex as an efficient catalyst for the heterogeneous Stille reaction. Tetrahedron 2008, 64, 7517. <http://dx.doi.org/10.1016/j.tet.2008.05.120>
  • Nishio Ryo, Sugiura Masaharu, Kobayashi Shu: Preparation of Phosphinated Polymer-Incarcerated Palladium and Its Application to CN and CC Bond-Forming Reactions. Chem Asian J 2007, 2, 983. <http://dx.doi.org/10.1002/asia.200700062>
  • Xu Qiuhua, Hao Wenyan, Cai Mingzhong: Mercapto-Functionalized MCM-41 Anchored Palladium(0) Complex as an Efficient Catalyst for the Heterogeneous Suzuki Reaction. Catal Lett 2007, 118, 98. <http://dx.doi.org/10.1007/s10562-007-9157-y>
  • Liu Gang, Cai Mingzhong: Synthesis of silica-supported selenide palladium(0) complex and its catalytic properties for phenylation of acid chlorides and aryl iodides or bromides. Catal Commun 2007, 8, 251. <http://dx.doi.org/10.1016/j.catcom.2006.06.015>
  • Cai Mingzhong, Sha Junchao, Xu Qiuhua: MCM-41-supported bidentate phosphine palladium(0) complex as an efficient catalyst for the heterogeneous Suzuki reaction. Journal of Molecular Catalysis A 2007, 268, 82. <http://dx.doi.org/10.1016/j.molcata.2006.12.011>
  • Cai Mingzhong, Xu Qiuhua, Huang Yixiang: Heterogeneous Suzuki reaction catalyzed by MCM-41-supported sulfur palladium(0) complex. Journal of Molecular Catalysis A 2007, 271, 93. <http://dx.doi.org/10.1016/j.molcata.2007.02.040>
  • Cai Mingzhong, Sha Junchao, Xu Qiuhua: MCM-41-supported bidentate phosphine palladium(0) complex: a highly active and recyclable catalyst for the Sonogashira reaction of aryl iodides. Tetrahedron 2007, 63, 4642. <http://dx.doi.org/10.1016/j.tet.2007.03.111>
  • Yamada Yoichi M. A.: Self-Assembled Complexes of Non-cross-linked Amphiphilic Polymeric Ligands with Inorganic Species: Highly Active and Reusable Solid-Phase Polymeric Catalysts. Chem Pharm Bull 2005, 53, 723. <http://dx.doi.org/10.1248/cpb.53.723>
  • YAMADA Yoichi M. A.: Development of Novel Solid-phase Polymeric Catalysts for Organic Syntheses. YAKUGAKU ZASSHI 2005, 125, 749. <http://dx.doi.org/10.1248/yakushi.125.749>
  • Mills Patrick L., Nicole Jacques F.: A novel reactor for high-throughput screening of gas–solid catalyzed reactions. Chem Eng Set 2004, 59, 5345. <http://dx.doi.org/10.1016/j.ces.2004.07.109>
  • Yamada Yoichi M.A, Takeda Koji, Takahashi Hideyo, Ikegami Shiro: Assembled catalyst of palladium and non-cross-linked amphiphilic polymer ligand for the efficient heterogeneous Heck reaction. Tetrahedron 2004, 60, 4097. <http://dx.doi.org/10.1016/j.tet.2004.02.068>
  • Clark Thomas, Landis Clark: Recent developments in chiral phospholane chemistry. Tet Asymm 2004, 15, 2123. <http://dx.doi.org/10.1016/j.tetasy.2004.06.025>
  • Berkowitz David B., Shen Weijun, Maiti Gourhari: In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination. Tet Asymm 2004, 15, 2845. <http://dx.doi.org/10.1016/j.tetasy.2004.06.052>
  • Berkowitz David B., Bose Mohua, Choi Sungjo: In Situ Enzymatic Screening (ISES): A Tool for Catalyst Discovery and Reaction Development. Angew. Chem. 2002, 114, 1673. <http://dx.doi.org/10.1002/1521-3757(20020503)114:9<1673::AID-ANGE1673>3.0.CO;2-K>
  • Herrmann Wolfgang A.: N-Heterocyclic Carbenes: A New Concept in Organometallic Catalysis. Angew Chem Int Ed 2002, 41, 1290. <http://dx.doi.org/10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y>
  • Berkowitz David B., Bose Mohua, Choi Sungjo: In Situ Enzymatic Screening (ISES): A Tool for Catalyst Discovery and Reaction Development. Angew. Chem. Int. Ed. 2002, 41, 1603. <http://dx.doi.org/10.1002/1521-3773(20020503)41:9<1603::AID-ANIE1603>3.0.CO;2-D>
  • Berkowitz David B., Bose Mohua, Choi Sungjo: In Situ Enzymatic Screening (ISES): A Tool for Catalyst Discovery and Reaction Development. Angew Chem Int Ed 2002, 41, 1603. <http://dx.doi.org/10.1002/1521-3773(20020503)41:9<1603::AID-ANIE1603>3.0.CO;2-D>
  • Finn M.G.: Emerging methods for the rapid determination of enantiomeric excess. Chirality 2002, 14, 534. <http://dx.doi.org/10.1002/chir.10101>