Platinum ethylene dimerization catalysts: Diphosphine vs. diimine ancillary ligand effects

Eisch, 2012, Fifty years of Ziegler-Natta polymerization: from serendipity to science. A personal account, Organometallics, 31, 4917, 10.1021/om300349x McDaniel, 2010, 291 Mulhaupt, 2003, Catalytic polymerization and post polymerization catalysis fifty years after the discovery of Ziegler’s catalysts, Macromol. Chem. Phys., 204, 289, 10.1002/macp.200290085 Bohm, 2003, The ethylene polymerization with Ziegler catalysts: fifty years after the discovery, Angew. Chem. Int. Ed., Eng., 42, 5010, 10.1002/anie.200300580 Clark, 1956, Marlex catalyst systems, Ind. Eng. Chem., 48, 1152, 10.1021/ie50559a021 Ziegler, 1955, Aluminum in organic chemistry. VII. Polymerization of ethylene and other olefins, Angew. Chem., 67, 426, 10.1002/ange.19550671610 Keim, 2013, Oligomerization of ethylene to α-olefins: discovery and development of the shell higher olefin process (SHOP), Angew. Chem. Int. Ed., 52, 12492, 10.1002/anie.201305308 Skupinska, 1991, Oligomerization of α-olefins to higher oligomers, Chem. Rev., 91, 613, 10.1021/cr00004a007 Ittel, 2000, Late-metal catalysts for ethylene homo- and copolymerization, Chem. Rev., 100, 1169, 10.1021/cr9804644 Johnson, 1995, “New Pd(II)- and Ni(II)-based catalysts for polymerization of ethylene and α-olefins, J. Am. Chem. Soc., 117, 6414, 10.1021/ja00128a054 Mecking, 1998, Mechanistic studies of the palladium-catalyzed copolymerization of ethylene and α-olefins with methyl acrylate, J. Am. Chem. Soc., 120, 888, 10.1021/ja964144i Killian, 1996, polymerization of α-olefins using NiII-α-diimine catalysts. Synthesis of new block polymers based on α-olefins”, J. Am. Chem. Soc., 118, 11664, 10.1021/ja962516h Shiotsuki, 2007, Mechanistic Studies of platinum(II)-catalyzed ethylene dimerization: determination of barriers to migratory insertion in diimine Pt(II) hydrido ethylene and ethyl ethylene intermediates, J. Am. Chem. Soc., 129, 4058, 10.1021/ja068118o White, 1999, Organometallics in acidic media: catalytic dimerization of ethylene by (Perfluoroalkyl)phosphine complexes of platinum and palladium in trifluoroacetic acid, Organometallics, 18, 2536, 10.1021/om990179q Basu, 2008, Synthesis of [(dfepe)Pt(Me)(NC5F5)]+ B(C6F5)4-, a highly active ethylene dimerization catalyst, Organometallics, 27, 3659, 10.1021/om8003509 Visalakshi, 1994, Synthesis and characterization of palladium(II) chloride and platinum(II) chloride complexes with substituted anilines, Synth. React. Inorg. Met.-Org. Chem., 24, 1043, 10.1080/00945719408001320 Pavlenko, 1982, IR-spectroscopic study of chloride complexes of platinum(II) and palladium(II) with perfluorinated aromatic amines, Koord. Khim., 8, 205 Vicente, 1996, Inorg. Chem., 35, 6592, 10.1021/ic951666a Goel, 1983, Preparation, characterization, and some reactions of hydridobis(tri-tert-butyl)phosphineplatinum(II) cation containing three-coordinate platinum, Can. J. Chem., 61, 1352, 10.1139/v83-238 Chisholm, 1973, Carbon-13 nuclear magnetic resonance studies. 35. Carbon-13 nuclear magnetic resonance studies of organometallic compounds. I. trans-Methylplatinum(II) derivatives, J. Am. Chem. Soc., 95, 8574, 10.1021/ja00807a013 Clark, 1971, Cationic organometallic complexes with unsaturated systems. I. Methylplatinum(II)-nitrile and -imino ether complexes, Inorg. Chem., 10, 2699, 10.1021/ic50106a015 Chisholm, 1971, Relations between carbon-13 nuclear magnetic resonance parameters, trans-influences, and ligand reactivities for methylplatinum compounds, J. Chem. Soc. D., 1627, 10.1039/c2971001627b McBee, 2008, Mechanistic studies of the hydroamination of norbornene with electrophilic platinum complexes: the role of proton transfer, J. Am. Chem. Soc., 130, 16562, 10.1021/ja8030104 Togo, 2019, Controlled cationic polymerization of 1-methoxy-1,3-butadiene: long-lived species-mediated reaction and control over microstructure with weak lewis bases, J. Polym. Sci., Part A: Polym. Chem., 57, 288, 10.1002/pola.29090 Brown, 1966, Preparation and reactions of 2,6-di-tert-butylpyridine and related hindered bases. A case of steric hindrance toward the proton, J. Am. Chem. Soc., 88, 986, 10.1021/ja00957a023 Parson, 2017, Organometallics in superacidic media: characterization of remarkably stable platinum-methyl bonds in HF/SbF5 solution, Organometallics, 36, 136, 10.1021/acs.organomet.6b00624 Romeo, 2006, Mechanistic insight into the protonolysis of the Pt-C bond as a model for C-H bond activation by platinum(II) complexes, Organometallics, 25, 3435, 10.1021/om060217n Schwartz, 1995, Interactions of cis-P2PtX2 complexes (X = H, Me) with Bis(pentamethylcyclopentadienyl)ytterbium, J. Am. Chem. Soc., 117, 6027, 10.1021/ja00127a016 Hietkamp, 1979, Ring size effects on some carbon-13, phosphorus-31 and platinum-195 NMR parameters in the series {Ph2P(CH2)nPh2}Pt(CH3)2, J. Organomet. Chem., 169, 107, 10.1016/S0022-328X(00)81461-8 Appleton, 1976, “Effect of chelate-ring size on spectroscopic and chemical properties of methylplatinum(II) complexes of the ditertiary phosphines phosphines Ph2P[CH2]nPPh2 (n = 1,2 or 3), J. Chem. Soc., Dalton Trans., 439, 10.1039/dt9760000439 Merwin, 1992, Kinetics and mechanism of biaryl reductive elimination from electron-poor platinum complexes [(C6F5)2PCH2CH2P(C6F5)2]Pt(Ar)2, Organometallics, 11, 2972, 10.1021/om00045a008 Chien, 1991, Isospecific polymerization of propylene catalyzed by rac-ethylenebis(indenyl)methylzirconium cation, J. Am. Chem. Soc., 113, 8570, 10.1021/ja00022a081 Hutton, 1983, [Pt2Me2(μ-Ph2PCH2PPh2)2][BF4]2, a highly reactive and coordinatively unsaturated diplatinum(II) complex. Crystal structures of [Pt2Me2L2(μ-Ph2PCH2PPh2)2][BF4]2 (L = acetonitrile or carbon monoxide), J. Chem. Soc., Chem. Commun., 1053, 10.1039/C39830001053 Houlis, 1998, Organometallics in superacidic media: generation of highly electrophilic (Fluoroalkyl)phosphine Pt(II) cationic complexes, J. Am. Chem. Soc., 120, 11020, 10.1021/ja9820487 Mayer, 2007, Bond order and valence indices: a personal account, J. Comp. Chem., 28, 204, 10.1002/jcc.20494 Costa, 1997, [(1,2,5,6-η)-1,5-Cyclooctadiene]dimethylplatinum(II), Inorg. Synth., 31, 284, 10.1002/9780470132623.ch49 Clark, 1973, Reactions of (π-1,5-cyclooctadiene)organoplatinum(II) compounds and the synthesis of perfluoroalkylplatinum complexes, J. Organomet. Chem., 59, 411, 10.1016/S0022-328X(00)95058-7 Peters, 1998, Activation of aromatic C-H bonds by (dmpe)Pt(Me)X (X = Me, O2CCF3, OTf) systems, Organometallics, 17, 4493, 10.1021/om980334l Alexander, 1963, Chemistry of decaborane-phosphorus compounds. IV. Monomeric, oligomeric, and cyclic phosphinocarboranes, Inorg. Chem., 2, 1107, 10.1021/ic50010a006 Kumada, 1973, Silicon hydrides and nickel complexes. III. Hydrosilylation of olefins with dichloro[1,2-bis(dimethylphosphino)-1,2-dicarba-closo-dodecaborane]nickel(II) as catalyst, J. Organomet. Chem., 50, 319, 10.1016/S0022-328X(00)95118-0 Reed, 1999, Isolation of protonated arenes (Wheland Intermediates) with BArF and carborane anions. A novel crystalline superacid, J. Am. Chem. Soc., 121, 6314, 10.1021/ja981861z Olah, 1972, Preparative carbocation chemistry. IV. Improved preparation of triphenylcarbenium (trityl) salts, Synthesis, 544 Gaussian 09, Revision A.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2009. Zhao, 2006, A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions, J. Chem. Phys., 125, 10.1063/1.2370993 Weigend, 2005, Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy, Phys. Chem. Chem. Phys., 7, 3297, 10.1039/b508541a Andrae, 1990, Energy-adjusted ab initio pseudopotentials for the second and third row transition elements, Theor. Chim. Acta, 77, 123, 10.1007/BF01114537