Login Register Cart 0
Generic placeholder image

Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Preparation of Palladium(II) Complexes of 1-substituted-3-phospholene Ligands and their Evaluation as Catalysts in Hydroalkoxycarbonylation

Author(s): Péter Bagi*, Réka Herbay, Gábor Györke, Péter Pongrácz, László Kollár, István Timári, László Drahos and György Keglevich

Volume 23, Issue 25, 2019

Page: [2873 - 2879] Pages: 7

DOI: 10.2174/1385272823666191204151311

Abstract

A series of palladium(II) complexes incorporating 1-substituted-3-methyl-3- phospholenes as the P-ligands were prepared from phospholene oxides by deoxygenation followed by complexation with PdCl2(PhCN)2. The two 1-substituted-3-methyl-3- phospholene ligands were trans position to each other in the Pd(II)-complexes. As the ligands contain a P-stereogenic center, the Pd-complexes were obtained as a 1:1 mixture of two stereoisomers, the homochiral (R,R and S,S) and the meso (R,S) forms, when racemic starting materials were used. An optically active Pd-complex containing (R)-1-propyl- 3-phospholene ligand was also prepared. Catalytic activity of an aryl- and an alkyl-3- phospholene-palladium(II)-complex was evaluated in hydroalkoxycarbonylation of styrene. The alkyl-derivative showed higher activity and selectivity towards the formation of the esters of 3-phenylpropionic acid. However, the overall activity of these PdCl2(phospholene)2-type complexes was low.

Keywords: 3-Phospholene oxides, deoxygenation, 3-phospholenes, palladium complexes, hydroalkoxycarbonylation.

« Previous
Graphical Abstract

[1]
Börner, A., Ed.; Phosphorus Ligands in Asymmetric Catalysis; Wiley: Weinheim, 2008.
[2]
Kamer, P.C.J.; Van Leeuwen, P.W.N.M., Eds.; Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis; Wiley: New York, 2012.
[http://dx.doi.org/10.1002/9781118299715]
[3]
Mathey, F., Ed.; Phosphorus-Carbon Heterocyclic Chemistry - The Rise of a New Domain; Elsevier: Amsterdam, 2001.
[4]
Kollár, L.; Keglevich, G. P-heterocycles as ligands in homogeneous catalytic reactions. Chem. Rev., 2010, 110(7), 4257-4302.
[http://dx.doi.org/10.1021/cr900364c] [PMID: 20384342]
[5]
Baber, R.A.; Haddow, M.F.; Middleton, A.J.; Orpen, A.G.; Pringle, P.G.; Haynes, A.; Williams, G.L.; Papp, R. Ligand stereoelectronic effects in complexes of phospholanes, phosphinanes, and phosphepanes and their implications for hydroformylation catalysis. Organometallics, 2007, 26, 713-725.
[http://dx.doi.org/10.1021/om060912v]
[6]
Carreira, M.; Charernsuk, M.; Eberhard, M.; Fey, N.; van Ginkel, R.; Hamilton, A.; Mul, W.P.; Orpen, A.G.; Phetmung, H.; Pringle, P.G. Anatomy of phobanes. diastereoselective synthesis of the three isomers of n-butylphobane and a comparison of their donor properties. J. Am. Chem. Soc., 2009, 131(8), 3078-3092.
[http://dx.doi.org/10.1021/ja808807s] [PMID: 19183007]
[7]
Fourmy, K.K.; Nguyen, D.H.; Dechy-Cabaret, O.; Gouygou, M. Phosphole-based ligands in catalysis. Catal. Sci. Technol., 2015, 5, 4289-4323.
[http://dx.doi.org/10.1039/C4CY01701C]
[8]
Burk, M.J. Modular phospholane ligands in asymmetric catalysis. Acc. Chem. Res., 2000, 33(6), 363-372.
[http://dx.doi.org/10.1021/ar990085c] [PMID: 10891054]
[9]
Clark, T.; Landis, C. Recent developments in chiral phospholane chemistry. Tetrahedron Asymmetry, 2004, 15, 2123-2137.
[http://dx.doi.org/10.1016/j.tetasy.2004.06.025]
[10]
Mathey, F.; Mercier, F.; Robin, F.; Ricard, L. From 2H-phospholes to BIPNOR, a new efficient biphosphine for asymmetric catalysis. J. Organomet. Chem., 1998, 557, 117-120.
[http://dx.doi.org/10.1016/S0022-328X(97)00739-0]
[11]
Zhou, Q-L., Ed.; Privileged Chiral Ligands and Catalysts; Wiley: Weinheim, 2011.
[http://dx.doi.org/10.1002/9783527635207]
[12]
Imamoto, T.; Oohara, N.; Takahashi, H. Optically Active 1,1′-Di- tert -butyl-2,2′-diphosphetanyl and its application in Rhodium-catalyzed asymmetric hydrogenations. Synthesis, 2004, 1353-1358.
[http://dx.doi.org/10.1055/s-2004-822396]
[13]
Imamoto, T.; Crépy, K.V.; Katagiri, K. Optically active 1,1′-di-tert-butyl-2,2′-dibenzophosphetenyl: a highly strained P-stereogenic diphosphine ligand. Tetrahedron Asymmetry, 2004, 15, 2213-2218.
[http://dx.doi.org/10.1016/j.tetasy.2004.05.041]
[14]
Bienewald, F.; Ricard, L.; Mercier, F.; Mathey, F. A new ligand containing a unique combination of backbone- and P-centered chirality: synthesis, resolution and asymmetric catalysis using a chiral enantiopure 2,2′-biphospholene. Tetrahedron Asymmetry, 1999, 10, 4701-4707.
[http://dx.doi.org/10.1016/S0957-4166(99)00547-9]
[15]
Wang, F.; Wang, Y.; Polavarapu, P.L.; Li, T.; Drabowicz, J.; Pietrusiewicz, K.M.; Zygo, K. Absolute configuration of tert-butyl-1-(2-methylnaphthyl)phosphine oxide. J. Org. Chem., 2002, 67(18), 6539-6541.
[http://dx.doi.org/10.1021/jo025908h] [PMID: 12201778]
[16]
Tang, W.; Zhang, X. A chiral 1,2-bisphospholane ligand with a novel structural motif: applications in highly enantioselective Rh-catalyzed hydrogenations. Angew. Chem. Int. Ed. Engl., 2002, 41(9), 1612-1614.
[http://dx.doi.org/10.1002/1521-3773(20020503)41:9<1612:AID-ANIE1612>3.0.CO;2-H] [PMID: 19750683]
[17]
Liu, D.; Zhang, X. Practical P-chiral phosphane ligand for Rh-catalyzed asymmetric hydrogenation. Eur. J. Org. Chem., 2005, 2005(4), 646-649.
[http://dx.doi.org/10.1002/ejoc.200400690]
[18]
Zhang, X.; Huang, K.; Hou, G.; Cao, B.; Zhang, X. Electron-donating and rigid P-stereogenic bisphospholane ligands for highly enantioselective rhodium-catalyzed asymmetric hydrogenations. Angew. Chem. Int. Ed. Engl., 2010, 49(36), 6421-6424.
[http://dx.doi.org/10.1002/anie.201002990] [PMID: 20661983]
[19]
Tang, W.; Qu, B.; Capacci, A.G.; Rodriguez, S.; Wei, X.; Haddad, N.; Narayanan, B.; Ma, S.; Grinberg, N.; Yee, N.K.; Krishnamurthy, D.; Senanayake, C.H. Novel, tunable, and efficient chiral bisdihydrobenzooxaphosphole ligands for asymmetric hydrogenation. Org. Lett., 2010, 12(1), 176-179.
[http://dx.doi.org/10.1021/ol9025815] [PMID: 19950894]
[20]
Beller, M.; Bolm, C., Eds.; Transition Metals for Organic Synthesis, 2nd ed; Wiley: Weinheim, 2004.
[http://dx.doi.org/10.1002/9783527619405]
[21]
Cornils, B.; Herrmann, W.A.; Beller, M.; Paciello, R., Eds.; Applied Homogeneous Catalysis with Organometallic Compounds, 3rd ed; Wiley: Weinheim, 2017.
[http://dx.doi.org/10.1002/9783527651733]
[22]
Franke, R.; Selent, D.; Börner, A. Applied hydroformylation. Chem. Rev., 2012, 112(11), 5675-5732.
[http://dx.doi.org/10.1021/cr3001803] [PMID: 22937803]
[23]
Wu, X-F.; Neumann, H.; Beller, M. Synthesis of heterocycles via palladium-catalyzed carbonylations. Chem. Rev., 2013, 113(1), 1-35.
[http://dx.doi.org/10.1021/cr300100s] [PMID: 23039127]
[24]
Del-Río, I.; Ruiz, N.; Claver, C.; van der Veen, L.A.; van Leeuwen, P.W.N.M. Hydroxycarbonylation of styrene with palladium catalysts. J. Mol. Catal. Chem., 2000, 161, 39-48.
[http://dx.doi.org/10.1016/S1381-1169(00)00359-9]
[25]
Kiss, G. Palladium-catalyzed reppe carbonylation. Chem. Rev., 2001, 101(11), 3435-3456.
[http://dx.doi.org/10.1021/cr010328q] [PMID: 11840990]
[26]
Godard, C.; Muñoz, B.K.; Ruiz, A.; Claver, C. Pd-catalysed asymmetric mono- and bis-alkoxycarbonylation of vinylarenes. Dalton Trans., 2008, (7), 853-860.
[http://dx.doi.org/10.1039/B714809G] [PMID: 18259615]
[27]
Muñoz, B.; Marinetti, A.; Ruiz, A.; Castillon, S.; Claver, C. Enhanced regioselectivity in palladium-catalysed asymmetric methoxycarbonylation of styrene using phosphetanes as chiral ligands. Inorg. Chem. Commun., 2005, 8, 1113-1115.
[http://dx.doi.org/10.1016/j.inoche.2005.09.006]
[28]
Muñoz, B.K.; Godard, C.; Marinetti, A.; Ruiz, A.; Benet-Buchholz, J.; Claver, C. Pd-catalysed methoxycarbonylation of vinylarenes using chiral monodentate phosphetanes and phospholane as ligands. Effect of substrate substituents on enantioselectivity. Dalton Trans., 2007, (47), 5524-5530.
[http://dx.doi.org/10.1039/b705230h] [PMID: 18043812]
[29]
Keglevich, G.; Kégl, T.; Odinets, I.L.; Vinogradova, N.M.; Kollár, L. Carbonylation reactions catalysed by rhodium(III) and palladium(II) complexes containing novel phosphine ligands. C. R. Chim., 2004, 7, 779-784.
[http://dx.doi.org/10.1016/j.crci.2004.02.013]
[30]
Odinets, I.L.; Vinogradova, N.M.; Lyssenko, K.A.; Golovanov, D.G.; Petrovskii, P.V.; Mastryukova, T.A.; Szelke, H.; Szabó, N.B.; Keglevich, G. Rhodium(III) and palladium(II) complexes of some P-heterocycles; synthesis and X-ray structures. J. Organomet. Chem., 2005, 690, 704-712.
[http://dx.doi.org/10.1016/j.jorganchem.2004.08.051]
[31]
Keglevich, G.; Bagi, P.; Szöllősy, Á.; Körtvélyesi, T.; Pongrácz, P.; Kollár, L.; Drahos, L. Platinum(II) complexes incorporating racemic and optically active 1-alkyl-3-phospholenes and 1-propyl-phospholane P-ligands: synthesis, stereostructure, NMR properties and catalytic activity. J. Organomet. Chem., 2011, 696, 3557-3563.
[http://dx.doi.org/10.1016/j.jorganchem.2011.08.006]
[32]
Bagi, P.; Kovács, T.; Szilvási, T.; Pongrácz, P.; Kollár, L.; Drahos, L.; Fogassy, E.; Keglevich, G. Platinum(II) complexes incorporating racemic and optically active 1-alkyl-3-phospholene P-ligands: synthesis, stereostructure, NMR properties and catalytic activity. J. Organomet. Chem., 2014, 751, 306-313.
[http://dx.doi.org/10.1016/j.jorganchem.2013.03.045]
[33]
Bagi, P.; Szilvási, T.; Pongrácz, P.; Kollár, L.; Drahos, L.; Keglevich, G. Platinum(II) complexes incorporating racemic and optically active 1-aryl-3- phospholene p-ligands as potential catalysts in hydroformylation. Curr. Org. Chem., 2014, 18, 1529-1538.
[http://dx.doi.org/10.2174/1385272819666140609224751]
[34]
Bagi, P.; Juhász, K.; Timári, I.; Kövér, K.E.; Mester, D.; Kállay, M.; Kubinyi, M.; Szilvási, T.; Pongrácz, P.; Kollár, L.; Karaghiosoff, K.; Czugler, M.; Drahos, L.; Fogassy, E.; Keglevich, G. A study on the optical resolution of 1-isopropyl-3-methyl-3-phospholene 1-oxide and its use in the synthesis of borane and platinum complexes. J. Organomet. Chem., 2015, 797, 140-152.
[http://dx.doi.org/10.1016/j.jorganchem.2015.08.013]
[35]
Herbay, R.; Péczka, N.; Györke, G.; Bagi, P.; Fogassy, E.; Keglevich, G. Isomerization and application of phospholene oxides. Phosphorus Sulfur Silicon Relat. Elem., 2019, 194, 610-613.
[http://dx.doi.org/10.1080/10426507.2018.1553043]
[36]
Novák, T.; Ujj, V.; Schindler, J.; Czugler, M.; Kubinyi, M.; Mayer, Z.A.; Fogassy, E.; Keglevich, G. Resolution of 1-substituted-3-methyl-3-phospholene 1-oxides by molecular complex formation with TADDOL derivatives. Tetrahedron Asymmetry, 2007, 18, 2965-2972.
[http://dx.doi.org/10.1016/j.tetasy.2007.11.028]
[37]
Keglevich, G.; Petneházy, I.; Miklós, P.; Almásy, A.; Tóth, G.; Tőke, L.; Quin, L.D. Ring expansion in the addition of dichlorocarbene to 2,5-dihydro-1H-phosphole 1-oxides. J. Org. Chem., 1987, 52, 3983-3986.
[http://dx.doi.org/10.1021/jo00227a008]
[38]
Keglevich, G.; Szelke, H.; Bálint, Á.; Imre, T.; Ludányi, K.; Nagy, Z.; Hanusz, M.; Simon, K.; Harmat, V. Tőke Fragmentation-related phosphinylations using 2-aryl-2-phosphabicyclo[2.2.2]oct- 5-ene- and -octa-5,7-diene 2-oxides. Heteroatom Chem., 2003, 14, 443-451.
[http://dx.doi.org/10.1002/hc.10176]
[39]
Kovács, T.; Urbanics, A.; Csatlós, F.; Keglevich, G. A study on the deoxygenation of trialkyl-, dialkyl-phenyl- and alkyl-diphenyl phosphine oxides by hydrosilanes. Heteroatom Chem., 2017, 28e21376
[http://dx.doi.org/10.1002/hc.21376]
[40]
Herbay, R.; Bagi, P.; Mucsi, Z.; Mátravölgyi, B.; Drahos, L.; Fogassy, E.; Keglevich, G. A novel preparation of chlorophospholenium chlorides and their application in the synthesis of phospholene boranes. Tetrahedron Lett., 2017, 58, 458-461.
[http://dx.doi.org/10.1016/j.tetlet.2016.12.059]
[41]
Grim, S.O.; Keiter, R.L. A phosphorus-31 magnetic resonance study of tertiary phosphine palladium(II) compounds. Inorg. Chim. Acta, 1970, 4, 56-60.
[http://dx.doi.org/10.1016/S0020-1693(00)93239-0]
[42]
Csók, Z.; Keglevich, G.; Petőcz, G.; Kollár, L. Platinum complexes of phospholes with reduced pyramidal character from Steric crowding. Inorg. Chem., 1999, 38(4), 831-833.
[http://dx.doi.org/10.1021/ic980963n] [PMID: 11670850]
[43]
Bagi, P.; Ujj, V.; Czugler, M.; Fogassy, E.; Keglevich, G. Resolution of P-stereogenic P-heterocycles via the formation of diastereomeric molecular and coordination complexes (a review). Dalton Trans., 2016, 45(5), 1823-1842.
[http://dx.doi.org/10.1039/C5DT02999F] [PMID: 26564410]
[44]
Hérault, D.; Nguyen, D.H.; Nuel, D.; Buono, G. Reduction of secondary and tertiary phosphine oxides to phosphines. Chem. Soc. Rev., 2015, 44(8), 2508-2528.
[http://dx.doi.org/10.1039/C4CS00311J] [PMID: 25714261]
[45]
Armarego, W.L.F. Purification of Laboratory Chemicals, 8th ed; Butterworth-Heinemann: Oxford, 2017.
[46]
Shriver, D.F.; Drezdzon, M.A. The Manipulation of Air-Sensitive Compounds, 2nd ed; Wiley: New York, 1986.

Rights & Permissions Print Cite
Article Metrics
11
1
© 2024 Bentham Science Publishers | Privacy Policy