Copyright (c) 2024 Deep Prakash Deep, Bhawana Pant, Priyanka Sagar
This work is licensed under a Creative Commons Attribution 4.0 International License.
Hydroformylation of Terminal Alkenes with in situ Generation of Syngas using Schiff Base Palladium Complex under Microwave and Conventional Heating
Corresponding Author(s) : D. Prakash
Asian Journal of Chemistry,
Vol. 36 No. 6 (2024): Vol 36 Issue 6, 2024
Abstract
Hydroformylation of alkenes and alkynes without syngas is preferred for obtaining valuable aldehydes with 100% atom economy using widely available components. Regarding selectivity, atom economy and energy efficiency, microwave-promoted catalytic hydroformylation reactions are the substitutes for conventional techniques. This is compatible with an increasing demand for more environmentally friendly industrial processes. In present work, Schiff base palladium complexes were utilized as catalysts for the hydroformylation of terminal alkenes using glyoxylic acid and formaldehyde as sources of CO and H2. Highly regio- and chemoselective olefin to aldehyde transfer hydroformylation of organic substrate in terminal unsaturated C-C bonds with microwave assistance in situ generation of syngas condition. Additionally, eight entries were hydroformylated to the linear aldehyde utilizing a palladium complex containing (E)-4-((4-nitrobenzylidene)-amino)phenol ligand under microwave and conventional heating, resulting in very high regioselectivity (l/b). Without CO and H2 cylinders, this proposed approach produced aldehydes with a 93% yield and excellent regioselectivity. Hydroformylation of terminal alkene, when carried out with palladium catalyst using glyoxylic acid as a source of CO and H2 and microwave-irradiated for 18-20 min at 160 ºC, led to the formation of the corresponding aldehyde without the formation of isomerized alkenes. During the hydroformylation process, the use of microwave and conventional heating techniques were compared and differentiated. The results demonstrated that microwave heating requires significantly lower temperatures and offers higher yields than traditional heating.
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- H. Alper and M. Vasylyev, Synthesis, 17, 2893 (2010); https://doi.org/10.1055/s-0030-1258169
- S. Ciceri, P. Ferraboschi, P. Grisenti, S. Reza Elahi, C. Castellano, M. Mori and F. Meneghetti, Catalysts, 10, 941 (2020); https://doi.org/10.3390/catal10080941
- B. Breit, Acc. Chem. Res., 36, 264 (2003); https://doi.org/10.1021/ar0200596
- A. Riisager, K.M. Eriksen, J. Hjortkjær and R. Fehrmann, J. Mol. Catal. Chem., 193, 259 (2003); https://doi.org/10.1016/S1381-1169(02)00471-5
- C.-F. Huo, Y.-W. Li, M. Beller and H. Jiao, Organometallics, 23, 765 (2014); https://doi.org/10.1021/om034212r
- J. Pospech, I. Fleischer, R. Franke, S. Buchholz and M. Beller, Angew. Chem. Int. Ed., 52, 2852 (2013); https://doi.org/10.1002/anie.201208330
- S. Siangwata, S. Chulu, C.L. Oliver and G.S. Smith, Appl. Organomet. Chem., 31, 3593 (2017); https://doi.org/10.1002/aoc.3593
- P. Pongrácz, I.D. Kostas and L. Kollár, J. Organomet. Chem., 723, 149 (2013); https://doi.org/10.1016/j.jorganchem.2012.10.018
- C. Chapuis and D. Jacoby, Appl. Catal. A Gen., 221, 93 (2001); https://doi.org/10.1016/S0926-860X(01)00798-0
- D. Konya, K.Q. Almeida Leñero and E. Drent, Organometallics, 25, 3166 (2006); https://doi.org/10.1021/om0601293
- G. Oehme, Angew. Chem. Int. Ed., 46, 8327 (2007); https://doi.org/10.1002/anie.200785530
- V. Ferraro, L. Genesin, J. Castro, L. Pietrobon, A. Vavasori and M. Bortoluzzi, J. Organomet. Chem., 993, 122711 (2023); https://doi.org/10.1016/j.jorganchem.2023.122711
- E. Petricci, A. Mann, J. Salvadori and M. Taddei, Tetrahedron Lett., 48, 8501 (2007); https://doi.org/10.1016/j.tetlet.2007.09.154
- E. Airiau, N. Girard, M. Pizzeti, J. Salvadori, M. Taddei and A. Mann, J. Org. Chem., 75, 8670 (2010); https://doi.org/10.1021/jo101776y
- T. Morimoto and K. Kakiuchi, Angew. Chem. Int. Ed., 43, 5580 (2004); https://doi.org/10.1002/anie.200301736
- M. Taddei, E. Cini, E. Airiau, N. Girard, A. Mann and J. Salvadori, Synlett, 02, 199 (2011); https://doi.org/10.1055/s-0030-1259281
- D.N. Gorbunov, M.V. Nenasheva, Y.S. Kardasheva and E.A. Karakhanov, Russ. Chem. Bull., 69, 625 (2020); https://doi.org/10.1007/s11172-020-2810-y
- W. Ren, W. Chang, J. Dai, Y. Shi, J. Li and Y. Shi, J. Am. Chem. Soc., 138, 14864 (2016); https://doi.org/10.1021/jacs.6b10297
- V.M. Jiménez-Pérez, B.M. Muñoz-Flores, L.M. Blanco Jerez, A. Gómez, L. D. Rangel, R. Chan-Navarro, N.Waksman, R. Ramírez-Durón, Int. J. Electrochem. Sci., 9, 7431 (2014); https://doi.org/10.1016/S1452-3981(23)10978-3
- K.V. Sharma, V. Sharma, R.K. Dubey and U.N. Tripathi, J. Coord. Chem., 62, 493 (2009); https://doi.org/10.1080/00958970802233136
- A. Hajri, W. Smirani and R. Abderrahim, Spectrochim. Acta A Mol. Biomol. Spectrosc., 79, 1856 (2011); https://doi.org/10.1016/j.saa.2011.05.075
- E.T. Shamkhy, J. Al-Nahrain Univ., 18, 39 (2015).
- E. Boymans, M. Janssen, C. Müller, M. Lutz and D. Vogt, Dalton Trans., 42, 137 (2013); https://doi.org/10.1039/C2DT31738A
- Y. Liu, L. Cai, S. Xu, W. Pu and X. Tao, Chem. Commun., 54, 2166 (2018); https://doi.org/10.1039/C7CC09629A
References
H. Alper and M. Vasylyev, Synthesis, 17, 2893 (2010); https://doi.org/10.1055/s-0030-1258169
S. Ciceri, P. Ferraboschi, P. Grisenti, S. Reza Elahi, C. Castellano, M. Mori and F. Meneghetti, Catalysts, 10, 941 (2020); https://doi.org/10.3390/catal10080941
B. Breit, Acc. Chem. Res., 36, 264 (2003); https://doi.org/10.1021/ar0200596
A. Riisager, K.M. Eriksen, J. Hjortkjær and R. Fehrmann, J. Mol. Catal. Chem., 193, 259 (2003); https://doi.org/10.1016/S1381-1169(02)00471-5
C.-F. Huo, Y.-W. Li, M. Beller and H. Jiao, Organometallics, 23, 765 (2014); https://doi.org/10.1021/om034212r
J. Pospech, I. Fleischer, R. Franke, S. Buchholz and M. Beller, Angew. Chem. Int. Ed., 52, 2852 (2013); https://doi.org/10.1002/anie.201208330
S. Siangwata, S. Chulu, C.L. Oliver and G.S. Smith, Appl. Organomet. Chem., 31, 3593 (2017); https://doi.org/10.1002/aoc.3593
P. Pongrácz, I.D. Kostas and L. Kollár, J. Organomet. Chem., 723, 149 (2013); https://doi.org/10.1016/j.jorganchem.2012.10.018
C. Chapuis and D. Jacoby, Appl. Catal. A Gen., 221, 93 (2001); https://doi.org/10.1016/S0926-860X(01)00798-0
D. Konya, K.Q. Almeida Leñero and E. Drent, Organometallics, 25, 3166 (2006); https://doi.org/10.1021/om0601293
G. Oehme, Angew. Chem. Int. Ed., 46, 8327 (2007); https://doi.org/10.1002/anie.200785530
V. Ferraro, L. Genesin, J. Castro, L. Pietrobon, A. Vavasori and M. Bortoluzzi, J. Organomet. Chem., 993, 122711 (2023); https://doi.org/10.1016/j.jorganchem.2023.122711
E. Petricci, A. Mann, J. Salvadori and M. Taddei, Tetrahedron Lett., 48, 8501 (2007); https://doi.org/10.1016/j.tetlet.2007.09.154
E. Airiau, N. Girard, M. Pizzeti, J. Salvadori, M. Taddei and A. Mann, J. Org. Chem., 75, 8670 (2010); https://doi.org/10.1021/jo101776y
T. Morimoto and K. Kakiuchi, Angew. Chem. Int. Ed., 43, 5580 (2004); https://doi.org/10.1002/anie.200301736
M. Taddei, E. Cini, E. Airiau, N. Girard, A. Mann and J. Salvadori, Synlett, 02, 199 (2011); https://doi.org/10.1055/s-0030-1259281
D.N. Gorbunov, M.V. Nenasheva, Y.S. Kardasheva and E.A. Karakhanov, Russ. Chem. Bull., 69, 625 (2020); https://doi.org/10.1007/s11172-020-2810-y
W. Ren, W. Chang, J. Dai, Y. Shi, J. Li and Y. Shi, J. Am. Chem. Soc., 138, 14864 (2016); https://doi.org/10.1021/jacs.6b10297
V.M. Jiménez-Pérez, B.M. Muñoz-Flores, L.M. Blanco Jerez, A. Gómez, L. D. Rangel, R. Chan-Navarro, N.Waksman, R. Ramírez-Durón, Int. J. Electrochem. Sci., 9, 7431 (2014); https://doi.org/10.1016/S1452-3981(23)10978-3
K.V. Sharma, V. Sharma, R.K. Dubey and U.N. Tripathi, J. Coord. Chem., 62, 493 (2009); https://doi.org/10.1080/00958970802233136
A. Hajri, W. Smirani and R. Abderrahim, Spectrochim. Acta A Mol. Biomol. Spectrosc., 79, 1856 (2011); https://doi.org/10.1016/j.saa.2011.05.075
E.T. Shamkhy, J. Al-Nahrain Univ., 18, 39 (2015).
E. Boymans, M. Janssen, C. Müller, M. Lutz and D. Vogt, Dalton Trans., 42, 137 (2013); https://doi.org/10.1039/C2DT31738A
Y. Liu, L. Cai, S. Xu, W. Pu and X. Tao, Chem. Commun., 54, 2166 (2018); https://doi.org/10.1039/C7CC09629A