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Abstract
Water and zirconium(IV) as catalyst were found to be effective in the transformation of terminal aromatic alkyne to aromatic methyl ketone in the microwave. This terminal alkyne hydration reaction proceeded in excellent yield with Zr(cp)2Cl2. The reaction was moved efficiently in presence of electron donating or electron withdrawing substituent on aromatic ring. An eco-friendly synthesis of aldehyde by oxidative cleavage of nitroalkene was developed with Zr(cp)2Cl2 catalyst and water in microwave.
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References
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- D.G. Lee and T. Chen, Eds.: B.M. Trost, I. Fleming and S.V. Ley, Comprehensive Organic Synthesis, Pergamon: Oxford, p. 541 (1991).
- O. Bortolini, A.D. Nino, M. Fogagnolo, G. Fantin, L. Mariuolo and A. Tocci, Oxidative Cleavage of Nitroalkenes with Hydrogen Peroxide in Environmentally Acceptable Solvents, Chem. Lett., 36, 472 (2007); https://doi.org/10.1246/cl.2007.472
- During this oxidative cleavage reaction we observed a formation of inseparable more polar product.
- R.K. Arigela, S. Samala, R. Mahar, S.K. Shukla and B. Kundu, Synthesis of Triazolo Isoquinolines and Isochromenes from 2-Alkynyl-benzaldehyde via Domino Reactions under Transition-Metal-Free Conditions, J. Org. Chem., 78, 10476 (2013); https://doi.org/10.1021/jo401929q
References
M. Tobiszewski, M. Marc, A. Galuszka and J. Namiesnik, Green Chemistry Metrics with Special Reference to Green Analytical Chemistry, Molecules, 20, 10928 (2015); https://doi.org/10.3390/molecules200610928
M.B. Gawande, S.N. Shelke, R. Zboril and R.S. Varma, Microwave-Assisted Chemistry: Synthetic Applications for Rapid Assembly of Nanomaterials and Organics, Acc. Chem. Res., 47, 1338 (2014); https://doi.org/10.1021/ar400309b
T. Tachinami, T. Nishimura, R. Ushimaru, R. Noyori and H. Naka, Hydration of Terminal Alkynes Catalyzed by Water-Soluble Cobalt Porphyrin Complexes, J. Am. Chem. Soc., 135, 50 (2013); https://doi.org/10.1021/ja310282t
B. Rao, W. Zhang, L. Hu and M. Luo, Catalytic Desulfitative Homo-coupling of Sodium Arylsulfinates in Water using PdCl2 as the Recyclable Catalyst and O2 as the Terminal Oxidant, Green Chem., 14, 3436 (2012); https://doi.org/10.1039/c2gc36550b
E. Mizushima, K. Sato, T. Hayashi and M. Tanaka, Highly Efficient AuI-Catalyzed Hydration of Alkynes, Angew. Chem. Int. Ed., 41, 4563 (2002); https://doi.org/10.1002/1521-3773(20021202)41:23<4563::AID-ANIE4563>3.0.CO;2-U
L.W. Francisco, D.A. Moreno and J.D. Atwood, Synthesis, Characteri-zation and Reaction Chemistry of PtCl2[P(m-C6H4SO3Na)3]2, an Alkyne Hydration Catalyst, Organometallics, 20, 4237 (2001); https://doi.org/10.1021/om0104870
H. Kanemitsu, K. Uehara, S. Fukuzumi and S. Ogo, Isolation and Crystal Structures of Both Enol and Keto Tautomer Intermediates in a Hydration of an Alkyne-Carboxylic Acid Ester Catalyzed by Iridium Complexes in Water, J. Am. Chem. Soc., 130, 17141 (2008); https://doi.org/10.1021/ja807254d
Y. Fukuda, H. Shiragami, K. Utimoto and H. Nozaki, Synthesis of Substituted Furans by Palladium-Catalyzed Cyclization of Acetylenic Ketones, J. Org. Chem., 56, 5816 (1991); https://doi.org/10.1021/jo00020a024
X.F. Wu, D. Bezier and C. Darcel, Development of the First Iron Chloride-Catalyzed Hydration of Terminal Alkynes, Adv. Synth. Catal., 351, 367 (2009); https://doi.org/10.1002/adsc.200800666
M.B.T. Thuong, A. Mann and A. Wagner, Mild Chemo-Selective Hydration of Terminal Alkynes Catalysed by AgSbF6, Chem. Commun., 48, 434 (2012); https://doi.org/10.1039/C1CC12928G
R. Das and D. Chakraborty, AgOTf Catalyzed Hydration of Terminal Alkynes, Appl. Organomet. Chem., 26, 722 (2012); https://doi.org/10.1002/aoc.2918
X. Jin, T. Oishi, K. Yamaguchi and N. Mizuno, Heterogeneously Catalyzed Efficient Hydration of Alkynes to Ketones by Tin–Tungsten Mixed Oxides, Chem. Eur. J., 17, 1261 (2011); https://doi.org/10.1002/chem.201002761
R. Casado, M. Contel, M. Laguna, P. Romero and S. Sanz, Organometallic Gold(III) Compounds as Catalysts for the Addition of Water and Methanol to Terminal Alkynes, J. Am. Chem. Soc., 125, 11925 (2003); https://doi.org/10.1021/ja036049x
N. Marion, R.S. Ramon and S.P. Nolan, [(NHC)AuI]-Catalyzed Acid-Free Alkyne Hydration at Part-Per-Million Catalyst Loadings, J. Am. Chem. Soc., 131, 448 (2009); https://doi.org/10.1021/ja809403e
A.S.K. Hashmi, T. Hengst, C. Lothschütz and F. Rominger, New and Easily Accessible Nitrogen Acyclic Gold(I) Carbenes: Structure and Application in the Gold-Catalyzed Phenol Synthesis as well as the Hydration of Alkynes, Adv. Synth. Catal., 352, 1315 (2010); https://doi.org/10.1002/adsc.201000126
N. Ghosh, S. Nayak and A.K. Sahoo, Gold-Catalyzed Regioselective Hydration of Propargyl Acetates Assisted by a Neighboring Carbonyl Group: Access to a-Acyloxy Methyl Ketones and Synthesis of (±)-Actinopolymorphol B, J. Org. Chem., 76, 500 (2011); https://doi.org/10.1021/jo101995g
P. Nun, R.S. Ramon, S. Gaillard and S.P. Nolan, Efficient Silver-Free Gold(I)-Catalyzed Hydration of Alkynes at Low Catalyst Loading, J. Organomet. Chem., 696, 7 (2011); https://doi.org/10.1016/j.jorganchem.2010.08.052
A. Leyva and A. Corma, Isolable Gold(I) Complexes having One Low-Coordinating Ligand as Catalysts for the Selective Hydration of Substituted Alkynes at Room Temperature without Acidic Promoters, J. Org. Chem., 74, 2067 (2009); https://doi.org/10.1021/jo802558e
N. Mugio, S. Mariusz, I. Hiroshi and S. Takumichi, Mercuric Triflate-TMU Catalyzed Hydration of Terminal Alkyne to give Methyl Ketone under Mild Conditions, Chem. Lett., 31, 12 (2002); https://doi.org/10.1246/cl.2002.12
T. Tsuchimoto, T. Joya, E. Shirakawa and Y. Kawakami, Brønsted Acid-Catalyzed Hydration of Alkynes: A Convenient Route to Diverse Carbonyl Compounds, Synlett, 12, 1777 (2000); https://doi.org/10.1055/s-2000-8707
D.G. Lee and T. Chen, Eds.: B.M. Trost, I. Fleming and S.V. Ley, Comprehensive Organic Synthesis, Pergamon: Oxford, p. 541 (1991).
O. Bortolini, A.D. Nino, M. Fogagnolo, G. Fantin, L. Mariuolo and A. Tocci, Oxidative Cleavage of Nitroalkenes with Hydrogen Peroxide in Environmentally Acceptable Solvents, Chem. Lett., 36, 472 (2007); https://doi.org/10.1246/cl.2007.472
During this oxidative cleavage reaction we observed a formation of inseparable more polar product.
R.K. Arigela, S. Samala, R. Mahar, S.K. Shukla and B. Kundu, Synthesis of Triazolo Isoquinolines and Isochromenes from 2-Alkynyl-benzaldehyde via Domino Reactions under Transition-Metal-Free Conditions, J. Org. Chem., 78, 10476 (2013); https://doi.org/10.1021/jo401929q