α-Arylation of β-diketones with aryl halides catalyzed by CuO/aluminosilicate
作者： S. Ganesh Babu , R. Sakthivel , N. Dharmaraj , R. Karvembu
DOI: 10.1016/J.TETLET.2014.10.098
关键词:
摘要: Abstract α-Arylation of β-diketones has been carried out over CuO/aluminosilicate catalyst under ligand-free condition. The reaction conditions were optimized with different solvents, bases, amounts, and temperatures using acetylacetone 4-bromobenzaldehyde as a model system. scope the catalytic system was extended to include various substituted aryl halides. 27 examples successfully demonstrated yields ranging from 55% 94%. C–Br bond regioselectively activated in presence C–Cl bond. Similarly chemoselectively arylated by dibenzoylacetone. Heterogeneous nature confirmed hot-filtration test. also found be reusable.
sci-hub.se 参考文章(33)
Mohd. Samim, N. K. Kaushik, Amarnath Maitra, Effect of size of copper nanoparticles on its catalytic behaviour in Ullman reaction Bulletin of Materials Science. ,vol. 30, pp. 535- 540 ,(2007) , 10.1007/S12034-007-0083-9
Mazaahir Kidwai, Saurav Bhardwaj, Roona Poddar, C-Arylation reactions catalyzed by CuO-nanoparticles under ligand free conditions Beilstein Journal of Organic Chemistry. ,vol. 6, pp. 35- 35 ,(2010) , 10.3762/BJOC.6.35
Neil A. Beare, John F. Hartwig, Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands. Journal of Organic Chemistry. ,vol. 67, pp. 541- 555 ,(2002) , 10.1021/JO016226H
Mehul B. Thathagar, Jurriaan Beckers, Gadi Rothenberg, Combinatorial Design of Copper‐Based Mixed Nanoclusters: New Catalysts for Suzuki Cross‐Coupling Advanced Synthesis & Catalysis. ,vol. 345, pp. 979- 985 ,(2003) , 10.1002/ADSC.200303045
Fangbin Gong, Qian Wang, Jun Chen, Zhipei Yang, Min Liu, Shayu Li, Guoqiang Yang, Ligang Bai, Jing Liu, Yuhui Dong, Exploring Intertrimer Cu···Cu Interactions and Further Phosphorescent Properties of Aryl Trimer Copper(I) Pyrazolates via Substituent Changing and External Pressure Inorganic Chemistry. ,vol. 49, pp. 1658- 1666 ,(2010) , 10.1021/IC9020417
Dequan Xiao, Lauren A. Martini, Robert C. Snoeberger, Robert H. Crabtree, Victor S. Batista, Inverse Design and Synthesis of acac-Coumarin Anchors for Robust TiO2 Sensitization Journal of the American Chemical Society. ,vol. 133, pp. 9014- 9022 ,(2011) , 10.1021/JA2020313
Christophe Provent, Pierre Chautemps, Jean-Louis Pierre, Screening of Various Procedures for the Oxidation of A 1,3-Diol with A 2-Benzylic Position; How to Obtain the 1,3-Diketone? Synthetic Communications. ,vol. 25, pp. 1907- 1912 ,(1995) , 10.1080/00397919508015866
M. Lakshmi Kantam, Soumi Laha, Jagjit Yadav, Suresh Bhargava, An efficient synthesis of propargylamines via three-component coupling of aldehydes, amines and alkynes catalyzed by nanocrystalline copper(II) oxide Tetrahedron Letters. ,vol. 49, pp. 3083- 3086 ,(2008) , 10.1016/J.TETLET.2008.03.053
Jafar Mohammad Nezhad, Jafar Akbari, Akbar Heydari, Behrooz Alirezapour, CuO Nanoparticles as an Efficient and Reusable Catalyst for the One-pot Friedlander Quinoline Synthesis Bulletin of The Korean Chemical Society. ,vol. 32, pp. 3853- 3854 ,(2011) , 10.5012/BKCS.2011.32.11.3853
Joseph B. Lambert, Zhongqiang Liu, Dinuclear Complexes and a One-dimensional Chain Involving Difunctional Ligands Containing the Acetylacetonate Functionality Journal of Chemical Crystallography. ,vol. 37, pp. 629- 639 ,(2007) , 10.1007/S10870-007-9224-7