Palladium-catalyzed dicarbonylation of 1,3-butadiene with bidentate phosphine ligands: A density functional theory study

doi:10.1016/j.cjche.2024.06.019

Abstract

Abstract: DFT calculations have been performed to discover the mechanism for the synthesis of dimethyl adipate (DMA) by 1,3-butadiene (BD) dicarbonylation catalyzed by a complex consisting of palladium and a bidentate diphosphine ligand. The computational results indicate that BD dicarbonylation involves two catalytic stages with the same reaction mechanism including terminal alkenyl insertion, CO migratory insertion, and methanolysis. Four different reaction routes have been explored, the pathway yielding linear DMA has the lowest alkenyl C-H insertion barrier with an overall barrier of 13.4 kcal·mol^-1 (1 kcal·mol^-1 = 4.184 kJ·mol^-1). The regioselectivity of the BD dicarbonylation depends mainly on the barrier of the alkenyl insertion into the palladium-hydrogen complex site. The computations well reproduced the experimentally observed linear selectivity.

Key words: 1,3-Butadiene, Dicarbonylation, DTBPX, DFT, Catalytic cycle

摘要： DFT calculations have been performed to discover the mechanism for the synthesis of dimethyl adipate (DMA) by 1,3-butadiene (BD) dicarbonylation catalyzed by a complex consisting of palladium and a bidentate diphosphine ligand. The computational results indicate that BD dicarbonylation involves two catalytic stages with the same reaction mechanism including terminal alkenyl insertion, CO migratory insertion, and methanolysis. Four different reaction routes have been explored, the pathway yielding linear DMA has the lowest alkenyl C-H insertion barrier with an overall barrier of 13.4 kcal·mol^-1 (1 kcal·mol^-1 = 4.184 kJ·mol^-1). The regioselectivity of the BD dicarbonylation depends mainly on the barrier of the alkenyl insertion into the palladium-hydrogen complex site. The computations well reproduced the experimentally observed linear selectivity.

关键词: 1,3-Butadiene, Dicarbonylation, DTBPX, DFT, Catalytic cycle

Zhongxian Yu, Jianhua Song, Dianhua Liu. Palladium-catalyzed dicarbonylation of 1,3-butadiene with bidentate phosphine ligands: A density functional theory study[J]. Chinese Journal of Chemical Engineering, 2024, 74(10): 92-99.

Zhongxian Yu, Jianhua Song, Dianhua Liu. Palladium-catalyzed dicarbonylation of 1,3-butadiene with bidentate phosphine ligands: A density functional theory study[J]. 中国化学工程学报, 2024, 74(10): 92-99.

References

[1] J.W. Liu, J. Yang, C. Schneider, R. Franke, R. Jackstell, M. Beller, Tailored palladium catalysts for selective synthesis of conjugated enynes by monocarbonylation of 1, 3-diynes, Angew. Chem. Int. Ed. 59 (23) (2020) 9032-9040.
[2] J. Liu, Q. Liu, R. Franke, R. Jackstell, M. Beller, Ligand-controlled palladium-catalyzed alkoxycarbonylation of allenes: Regioselective synthesis of α, β- and β, γ-unsaturated esters, J. Am. Chem. Soc. 137 (26) (2015) 8556-8563.
[3] A. Behr, M. Becker, T. Beckmann, L. Johnen, J. Leschinski, S. Reyer, Telomerization: Advances and applications of a versatile reaction, Angew. Chem. Int. Ed Engl. 48 (20) (2009) 3598-3614.
[4] F. Ferretti, M. Sharif, S. Dastgir, F. Ragaini, R. Jackstell, M. Beller, Selective palladium-catalysed synthesis of diesters: Alkoxycarbonylation of a CO₂-butadiene derived δ-lactone, Green Chem. 19 (15) (2017) 3542-3548.
[5] J. Mormul, J. Breitenfeld, O. Trapp, R. Paciello, T. Schaub, P. Hofmann, Synthesis of adipic acid, 1, 6-hexanediamine, and 1, 6-hexanediol via double-n-selective hydroformylation of 1, 3-butadiene, ACS Catal. 6 (5) (2016) 2802-2810.
[6] A.M. Silva, M.A. Morales, E.M. Baggio-Saitovitch, E. Jordao, M.A. Fraga, Selective hydrogenation of dimethyl adipate on titania-supported RuSn catalysts, Appl. Catal. A Gen. 353 (1) (2009) 101-106.
[7] H.B. Jiang, H.J. Jiang, K. Su, D.M. Zhu, X.L. Zheng, H.Y. Fu, H. Chen, R.X. Li, A Ru-Sn-Co/AlO(OH) as a highly efficient catalyst for hydrogenation of dimethyl adipate to 1, 6-hexanodiol in aqueous phase, Appl. Catal. A Gen. 447 (2012) 164-170.
[8] I.N. Vikhareva, G.K. Aminova, A.K. Mazitova, Ecotoxicity of the adipate plasticizers: Influence of the structure of the alcohol substituent, Molecules 26 (16) (2021) 4833.
[9] J. Yang, J.W. Liu, Y. Ge, W.H. Huang, F. Ferretti, H. Neumann, H.J. Jiao, R. Franke, R. Jackstell, M. Beller, Efficient palladium-catalyzed carbonylation of 1, 3-dienes: Selective synthesis of adipates and other aliphatic diesters, Angew. Chem. Int. Ed Engl. 60 (17) (2021) 9527-9533.
[10] M.H. Thiemens, W.C. Trogler, Nylon production: An unknown source of atmospheric nitrous oxide, Science 251 (4996) (1991) 932-934.
[11] Z.J. Bryan, A.C. Lee, Production of Unsaturated Monoesters by the Rhodium Catalyzed Carbonylation of Conjugated Diolefins, U.S. Pat., 4236023, 1964.
[12] C.K. Hsu, F. Dobinson, Dimethyl Adipate from Butadiene, U.S. Pat., 3161672, 1986.
[13] E.M. Atadan, H.S. Bruner Jr., Process for the Preparation of Adipic Acid or Pentenoic Acid, U.S. Pat., 5292944, 1994.
[14] E. Drent, W.W. Jager, Process for the Carbonylation of Conjugated Dienes, U.S. Pat., 6737542, 2004.
[15] J. Yang, J.W. Liu, Y. Ge, W.H. Huang, H. Neumann, R. Jackstell, M. Beller, Direct and selective synthesis of adipic and other dicarboxylic acids by palladium-catalyzed carbonylation of allylic alcohols, Angew. Chem. Int. Ed Engl. 59 (46) (2020) 20394-20398.
[16] Y. Zhao, D.G. Truhlar, Density functionals with broad applicability in chemistry, Acc. Chem. Res. 41 (2) (2008) 157-167.
[17] D.S. Sholl, J.A. Steckel, Density Functional Theory. Wiley, 2009.
[18] L. Crawford, D.J. Cole-Hamilton, E. Drent, M. Buhl, Mechanism of alkyne alkoxycarbonylation at a Pd catalyst with P, N hemilabile ligands: A density functional study, Chemistry 20 (43) (2014) 13923-13926.
[19] S. Ahmad, L.E. Crawford, M. Buhl, Palladium-catalysed methoxycarbonylation of ethene with bidentate diphosphine ligands: A density functional theory study, Phys. Chem. Chem. Phys. 22 (42) (2020) 24330-24336.
[20] R. Gholizadeh, Y.X. Yu, N₂O+CO reaction over Si- and Se-doped graphenes: An ab initio DFT study, Appl. Surf. Sci. 357 (2015) 1187-1195.
[21] J. Wu, J.H. Li, Y.X. Yu, Highly stable Mo-doped Fe₂P and Fe₃P monolayers as low-onset-potential electrocatalysts for nitrogen fixation, Catal. Sci. Technol. 11 (4) (2021) 1419-1429.
[22] Y.X. Yu, Theoretical insights into surface-phase transition and ion competition during alkali ion intercalation on the Cu₄Se₄ nanosheet, Phys. Chem. Chem. Phys. 26 (1) (2024) 323-335.
[23] M. Frisch, G. Trucks, H. B. Schlegel, G. Scuseria, M. Robb, J. Cheeseman, G. Scalmani, V. Barone, G. Petersson, and H. Nakatsuji, Gaussian 16, Gaussian, Inc. Wallingford, CT, 2016.
[24] C.R. Shen, X.F. Wu, Palladium-catalyzed carbonylative multicomponent reactions, Chemistry 23 (13) (2017) 2973-2987.
[25] V. Vetere, C. Adamo, P. Maldivi, Performance of the ‘parameter free’ PBE0 functional for the modeling of molecular properties of heavy metals, Chem. Phys. Lett. 325 (1-3) (2000) 99-105.
[26] A.D. Becke, Density-functional thermochemistry. IV. A new dynamical correlation functional and implications for exact-exchange mixing, J. Chem. Phys. 104 (3) (1996) 1040-1046.
[27] J.P. Perdew, J.A. Chevary, S.H. Vosko, K.A. Jackson, M.R. Pederson, D.J. Singh, C. Fiolhais, Atoms, molecules, solids, and surfaces: Applications of the generalized gradient approximation for exchange and correlation, Phys. Rev. B 46 (11) (1992) 6671-6687.
[28] C.A. Guido, E. Bremond, C. Adamo, P. Cortona, Communication: One third: A new recipe for the PBE0 paradigm, J. Chem. Phys. 138 (2) (2013) 021104.
[29] J.M. del Campo, J.L. Gazquez, S.B. Trickey, A. Vela, Non-empirical improvement of PBE and its hybrid PBE0 for general description of molecular properties, J. Chem. Phys. 136 (10) (2012) 104108.
[30] C. Adamo, M. Cossi, V. Barone, An accurate density functional method for the study of magnetic properties: The PBE0 model, J. Mol. Struct. THEOCHEM 493 (1-3) (1999) 145-157.
[31] P.L. Arnold, E. Hollis, G.S. Nichol, J.B. Love, J.C. Griveau, R. Caciuffo, N. Magnani, L. Maron, L. Castro, A. Yahia, S.O. Odoh, G. Schreckenbach, Oxo-functionalization and reduction of the uranyl ion through lanthanide-element bond homolysis: Synthetic, structural, and bonding analysis of a series of singly reduced uranyl-rare earth 5f1-4f(n) complexes, J. Am. Chem. Soc. 135 (10) (2013) 3841-3854.
[32] B. Barcs, L. Kollar, T. Kegl, Density functional study on the mechanism of nickel-mediated diazo carbonylation, Organometallics 31 (23) (2012) 8082-8097.
[33] C. Yang, M.S. Li, W.K. Dai, J. Wei, Q. Yang, Y. Feng, W.X. Yang, J. Ding, Y. Zheng, M.Y. Wang, X.B. Ma, Solvent effect on mechanistic pathways in Rh-catalyzed hydroformylation of formaldehyde, Mol. Catal. 524 (2022) 112248.
[34] M. Jain, J.R. Chelikowsky, S.G. Louie, Reliability of hybrid functionals in predicting band gaps, Phys. Rev. Lett. 107 (21) (2011) 216806.
[35] C. Legault, CYLview20: Visualization and analysis software for computational chemistry, CYLview, 2020.
[36] P. Roesle, C.J. Durr, H.M. Moller, L. Cavallo, L. Caporaso, S. Mecking, Mechanistic features of isomerizing alkoxycarbonylation of methyl oleate, J. Am. Chem. Soc. 134 (42) (2012) 17696-17703.
[37] W. Clegg, M. R. J. Elsegood, G. R. Eastham, R. P. Tooze, X.L. Wang, K. Whiston, Highly active and selective catalysts for the production of methyl propanoate via the methoxycarbonylation of ethene, Chem. Commun. (18) (1999) 1877-1878.
[38] P. Roesle, L. Caporaso, M. Schnitte, V. Goldbach, L. Cavallo, S. Mecking, A comprehensive mechanistic picture of the isomerizing alkoxycarbonylation of plant oils, J. Am. Chem. Soc. 136 (48) (2014) 16871-16881.
[39] C. Jimenez Rodriguez, D.F. Foster, G.R. Eastham, D.J. Cole-Hamilton, Highly selective formation of linear esters from terminal and internal alkenes catalysed by palladium complexes of bis-(di-tert-butylphosphinomethyl)benzene, Chem. Commun. (15) (2004) 1720-1721.
[40] M. Beller, A. Krotz, W. Baumann, Palladium-catalyzed methoxycarbonylation of 1, 3-butadiene: Catalysis and mechanistic studies, Adv. Synth. Catal. 344 (5) (2002) 517.