Efficient Oxidative Scission of Alkenes or Alkynes with Heterogeneous Ruthenium Zirconia Catalyst |
Irshad, Mobina
(Department Chemical Engineering, Kangwon National University)
Choi, Bong Gill (Department Chemical Engineering, Kangwon National University) Kang, Onyu (Department Chemical Engineering, Kangwon National University) Hong, Seok Bok (Department Chemical Engineering, Kangwon National University) Hwang, Sung Yeon (Korea Research Institute of Chemical Technology) Heo, Young Min (SKC Advanced Technology R&D Center) Kim, Jung Won (Department Chemical Engineering, Kangwon National University) |
1 | Y.-H. Kim, S.-Y. Hwang, J. W. Kim, and Y.-S. Lee, Zriconia supported ruthenium catalyst for efficient aerobic oxidation of alcohols to aldehydes, Ind. Chem. Eng. Res., 53, 12548-12552 (2014). DOI |
2 | N. M. Neisius and B. Plietke, Diastereoselective Ru-catalyzed cross-metathesis-dihydroxylation sequence: An efficient approach toward enantiomerically enriched syn-diols, J. Org. Chem., 73, 3218-3227 (2008). DOI |
3 | Z. Hong, L. Liu, M. Sugiyama, Y. Fu, and C. H. Wong, Concise synthesis of iminocyclitols via petasis-type aminocyclization, J. Am. Chem. Soc., 131, 8352-8353 (2009). DOI |
4 | A. Gao, F. Yang, J. Li, and Y. Wu, Pd/Cu-catalyzed oxidation of alkynes into 1,2-diketones using DMSO as the oxidant, Tetrahedron, 68, 4950-4954 (2012). DOI |
5 | Y. Xu and X. Wan, Ruthenium-catalyzed oxidation of alkynes to 1,2-diketones under room temperature and one-pot synthesis of quinoxalines, Tetrahedron Lett., 54, 642-645 (2013). DOI |
6 | P. Daw, R. Petakamsetty, A. Sarbajna, S. Laha, R. Ramapanicker, and J. K. Bera, A highly efficient catalyst for selective oxidative scission of olefins to aldehydes: Abnormal-NHC-Ru(II) complex in oxidation chemistry, J. Am. Chem. Soc., 136, 13987-13990 (2014). DOI |
7 | D. G. Lee and T. Chen, Comprehensive organic synthesis. In: P. Knochel and G. A. Molander (eds.). Cleavage Reactions, 541-591, Elsevier, Oxford, UK (1991). |
8 | V. V. Namboodiri, R. S. Varma, E. S. Demessie, and U. R Pillai, Selective oxidation of styrene to acetophenone in the presence of ionic liquids, Green Chem., 4, 170-173 (2002). DOI |
9 | I. V. Soares, E. G. Vieira, N. L. D. Filho, A. C. Bastos, N. C. da Silva, E. F. Garcia, and L. J. A. Lima, Adsorption of heavy metal ions and epoxidation catalysis using a new polyhedral oligomeric silsesquioxane, Chem. Eng. J., 218, 405-414 (2013). DOI |
10 | G. B. Dong, P. Teo, Z. K. Wickens, and R. H. Grubbs, Primary alcohols from terminal olefins: Formal anti-Markovnikov hydration via triple relay catalysis, Science, 333, 1609-1612 (2011). DOI |
11 | S. Chen, Z. Liu, E. Shi, L. Chen, W. Wei, H. Li, Y. Cheng, and X. Wan, Ruthenium catalyzed oxidation of alkenes at room temperature: A practical and concise approach to r-diketones, Org. Lett., 13, 2274-2277 (2011). DOI |
12 | Y. Nishiyama, Y. Nakagawa, and N. Mizuno, High turnover numbers for the catalytic selective epoxidation of alkenes with 1 atm of molecular oxygen, Angew. Chem. Int. Ed., 40, 3639-3641 (2001). DOI |
13 | M. R. Maurya, A. Kumar, and J. C. Pessoa, Vanadium complexes immobilized on solid supports and their use as catalysts for oxidation and functionalization of alkanes and alkenes, Coord. Chem. Rev., 255, 2315-2344 (2011). DOI |
14 | W. Jiang, J. D. Gorden, and C. R. Goldsmith, A homogeneous gallium (III) compound selectively catalyzes the epoxidation of alkenes, Inorg. Chem., 51, 2725-2727 (2012). DOI |
15 | P. Shringarpure and A. Patel, Cobalt (II) exchanged supported 12-tungstophosphoric acid: Synthesis, characterization and non-solvent liquid phase aerobic oxidation of alkenes, J. Mol. Catal. A, 321, 22-26 (2010). DOI |
16 | B. Travis, R. S. Narayan, and B. Borhan, Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: An organometallic ozonolysis, J. Am. Chem. Soc., 124, 3824-3825 (2002). DOI |
17 | M. Moghadam, V. Mirkhani, S. Angestaninejad, I. Mohammadpoor-Baltork, and M. M. Javadi, Molybdenum schiff base-polyoxometalate hybrid compound: A heterogeneous catalyst for alkene epoxidation with tert-BuOOH, Polyhedron, 29, 648-654 (2010). DOI |
18 | M. Vafaeezadeh and M. M. Hashemi, Dual catalytic function of the task-specific ionic liquid: Green oxidation of cyclohexene to adipic acid using 30% , Chem. Eng. J., 221, 254-257 (2013). DOI |
19 | B. Weiner, A. Baeza, T. Jerphagnon, and B. L. Feringa, Aldehyde selective wacker oxidations of phthalimide protected allylic amines: A new catalytic route to -amino acids, J. Am. Chem. Soc., 131, 9473-9474 (2009). DOI |
20 | S. Baskaran, S. J. Das, and S. Chandrasekaran, Heterogeneous permanganate oxidations: an improved procedure for the direct conversion of olefins to -diketones/-hydroxy ketones, J. Org. Chem., 54, 5182-5184 (1989). DOI |
21 | D. C. Whitehead, B. R. Travis, and B. Borhan, The -mediated oxidative cleavage of olefins catalyzed by alternative osmium sources, Tetrahedron Lett., 47, 3797-3800 (2006). DOI |
22 | O. Hiroshi, O. Kazuhiro, and B. Shinji, Use of the composite material as an environmentally benign solid catalyst for the oxidative cleavage of olefins, Synlett., 3201-3205 (2007). |
23 | M. O. F. Goulart, A. G. Cioletti, J. D. de Souza Filho, C. A. de Simone, E. E. Castellano, F. S. Emery, K. C. G. de Moura, M. C. F. R. Pintod, and A. V. Pinto, Unexpected oxidation of a substituted benzo[a]phenazine: Oxidative cleavage of a double bond and formation of a macrolactone, Tetrahedron Lett., 44, 3581-3585 (2003). DOI |
24 | D. Xing, B. Guan, G. Cai, Z. Fang, L. Yang, and Z. Shi, Gold(I)-catalyzed oxidative cleavage of a C-C double bond in water, Org. Lett., 8, 693-696 (2006). DOI |
25 | J. H. Noh, R. Patala, and R. Meijboom, Catalytic evaluation of dendrimer and reverse microemulsion template Pd and Pt nanoparticles for the selective oxidation of styrene using TBHP, Appl. Catal. A, 514, 253-266 (2016). DOI |