Suzuki Coupling Reactions Catalyzed with Palladacycles and Palladium(II) Complexes of 2‐Thiophenemethylamine‐Based Schiff Bases: Examples of Divergent Pathways for the Same Ligand
作者： Hemant Joshi , Om Prakash , Alpesh K Sharma , Kamal Nayan Sharma , Ajai K Singh
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摘要: Activation of Suzuki coupling with a complex palladium varies the mode coordination its ligand. The moisture-/air-insensitive palladacycles and complexes designed using same ligand (Schiff base, coordinating as an N,C– N,O– ligand, respectively) have been found to follow different pathways. Palladacycles are more efficient, their 0.001 mol-% loading gives good conversion (yield > 90 %) in several cases. Higher than this is required for Pd obtain similar yield. involves role nanosized Pd-containing species generated situ during catalysis, which, PdII complexes, no such particle formed Pd0 probably remains protected by sulfur thienyl group. Schiff bases used here were reaction 2-thiophenemethylamine 2-hydroxybenzophenone/2-hydroxy-4-methoxybenzophenone/2-hydroxyacetophenone (L1/L2/L3). Upon treatment [PdCl2(CH3CN)2] [Na2PdCl4] they gave [PdL1/L2(CH3CN)Cl] (1/3) palladium(II) [Pd(L1/L2/L3)2] (2/4/5), respectively. Compounds L1–L3 1–5 authenticated 1H 13C{1H} NMR spectroscopy, HRMS. Single crystal structures 1, 2, 4, 5 reveal nearly square-planar geometry around each case. PPh3/Hg poisoning two-phase tests indicate that catalysis homogeneous both palladacycle through leaching from NPs case former.
sci-hub.se 参考文章(49)
Jairton Dupont, Crestina S. Consorti, John Spencer, The potential of palladacycles: more than just precatalysts Chemical Reviews. ,vol. 105, pp. 2527- 2571 ,(2005) , 10.1021/CR030681R
Yoshiaki Kitamura, Satoko Sako, Takahiro Udzu, Azusa Tsutsui, Tomohiro Maegawa, Yasunari Monguchi, Hironao Sajiki, Ligand-free Pd/C-catalyzed Suzuki–Miyaura coupling reaction for the synthesis of heterobiaryl derivatives Chemical Communications. pp. 5069- 5071 ,(2007) , 10.1039/B712207A
Jun Hu, Yubiao Liu, Pd nanoparticle aging and its implications in the suzuki cross-coupling reaction. Langmuir. ,vol. 21, pp. 2121- 2123 ,(2005) , 10.1021/LA0471902
Sambasivarao Kotha, Kakali Lahiri, Dhurke Kashinath, Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis Tetrahedron. ,vol. 58, pp. 9633- 9695 ,(2002) , 10.1016/S0040-4020(02)01188-2
Adam F. Littke, Chaoyang Dai, Gregory C. Fu, Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions Journal of the American Chemical Society. ,vol. 122, pp. 4020- 4028 ,(2000) , 10.1021/JA0002058
Adam F. Littke, Gregory C. Fu, Palladium-Catalyzed Coupling Reactions of Aryl Chlorides Angewandte Chemie International Edition. ,vol. 41, pp. 4176- 4211 ,(2002) , 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
Sabrina M. Nobre, Adriano L. Monteiro, Pd complexes of iminophosphine ligands: A homogeneous molecular catalyst for Suzuki–Miyaura cross-coupling reactions under mild conditions Journal of Molecular Catalysis A-chemical. ,vol. 313, pp. 65- 73 ,(2009) , 10.1016/J.MOLCATA.2009.08.003
V. A. Kozlov, D. V. Aleksanyan, Yu. V. Nelyubina, K. A. Lyssenko, A. A. Vasil’ev, P. V. Petrovskii, I. L. Odinets, Cyclopalladation of meta-(Diphenylthiophosphoryloxy)benzaldimines: NCS and Unexpected NCO 5,6-Membered Pincer Palladium Complexes Organometallics. ,vol. 29, pp. 2054- 2062 ,(2010) , 10.1021/OM9009894
Cornelis A. Kruithof, Alexsandro Berger, Harmen P. Dijkstra, Fouad Soulimani, Tom Visser, Martin Lutz, Anthony L. Spek, Robertus J. M. Klein Gebbink, Gerard van Koten, Sulfato-bridged ECE-pincer palladium(II) complexes: structures in the solid-state and in solution, and catalytic properties Dalton Transactions. ,vol. 2009, pp. 3306- 3314 ,(2009) , 10.1039/B816936E
Arun Kumar, Gyandshwar Kumar Rao, Satyendra Kumar, Ajai K Singh, None, Organosulphur and related ligands in Suzuki–Miyaura C–C coupling Dalton Transactions. ,vol. 42, pp. 5200- 5223 ,(2013) , 10.1039/C2DT32432F