Pt-Ni alloy catalysts for highly selective anti-Markovnikov alkene hydrosilylation

Troegel D, Stohrer J. Recent advances and actual challenges in late transition metal catalyzed hydrosilylation of olefins from an industrial point of view. Coord Chem Rev, 2011, 255: 1440–1459 Marciniec B. Catalysis by transition metal complexes of alkene silylation–recent progress and mechanistic implications. Coord Chem Rev, 2005, 249: 2374–2390 Speier JL, Webster JA, Barnes GH. The addition of silicon hydrides to olefinic double bonds. Part II. The use of group VIII metal catalysts. J Am Chem Soc, 1957, 79: 974–979 Karstedt BD. General Electric, US Patent. 1973 Markó IE, Stérin S, Buisine O, et al. Selective and efficient platinum( 0)-carbene complexes as hydrosilylation catalysts. Science, 2002, 298: 204–206 Putzien S, Louis E, Nuyken O, et al. PtO2 as a “self-dosing” hydrosilylation catalyst. Catal Sci Technol, 2012, 2: 725–729 Hitchcock PB, Lappert MF, Warhurst NJW. Synthesis and structure of arac-tris(divinyldisiloxane) diplatinum(0) complex and its reaction with maleic anhydride. Angew Chem Int Ed Engl, 1991, 30: 438–440 Uozumi Y, Hayashi T. Catalytic asymmetric synthesis of optically active 2-alkanols via hydrosilylation of 1-alkenes with a chiral monophosphine-palladium catalyst. J Am Chem Soc, 1991, 113: 9887–9888 Itami K, Mitsudo K, Nishino A, et al. Metal-catalyzed hydrosilylation of alkenes and alkynes using dimethyl(pyridyl)silane. J Org Chem, 2002, 67: 2645–2652 Hu R, Hao W, Cai M. MCM-41-supported bidentate phosphine rhodium complex: an efficient and recyclable heterogeneous catalyst for the hydrosilylation of olefins. Chin J Chem, 2011, 29: 1629–1634 Nesmeyanov AN, Freidlina RK, Chukovskaya EC, et al. Addition, substitution, and telomerization reactions of olefins in the presence of metal carbonyls or colloidal iron. Tetrahedron, 1962, 17: 61–68 Mitchener JC, Wrighton MS. Photogeneration of very active homogeneous catalysts using laser light excitation of iron carbonyl precursors. J Am Chem Soc, 1981, 103: 975–977 Bart SC, Lobkovsky E, Chirik PJ. Preparation and molecular and electronic structures of iron(0) dinitrogen and silane complexes and their application to catalytic hydrogenation and hydrosilation. J Am Chem Soc, 2004, 126: 13794–13807 Russell SK, Darmon JM, Lobkovsky E, et al. Synthesis of arylsubstituted bis(imino)pyridine iron dinitrogen complexes. Inorg Chem, 2010, 49: 2782–2792 Wu JY, Stanzl BN, Ritter T. A strategy for the synthesis of welldefined iron catalysts and application to regioselective diene hydrosilylation. J Am Chem Soc, 2010, 132: 13214–13216 Hojilla Atienza CC, Tondreau AM, Weller KJ, et al. High-selectivity bis(imino)pyridine iron catalysts for the hydrosilylation of 1,2,4-trivinylcyclohexane. ACS Catal, 2012, 2: 2169–2172 Kamata K, Suzuki A, Nakai Y, et al. Catalytic hydrosilylation of alkenes by iron complexes containing terpyridine derivatives as ancillary ligands. Organometallics, 2012, 31: 3825–3828 Tondreau AM, Atienza CCH, Darmon JM, et al. Synthesis, electronic structure, and alkene hydrosilylation activity of terpyridine and bis(imino)pyridine iron dialkyl complexes. Organometallics, 2012, 31: 4886–4893 Peng D, Zhang Y, Du X, et al. Phosphinite-iminopyridine iron catalysts for chemoselective alkene hydrosilylation. J Am Chem Soc, 2013, 135: 19154–19166 Greenhalgh MD, Frank DJ, Thomas SP. Iron-catalysed chemo-, regio-, and stereoselective hydrosilylation of alkenes and alkynes using a bench-stable iron(II) pre-catalyst. Adv Synth Catal, 2014, 356: 584–590 Tondreau AM, Atienza CCH, Weller KJ, et al. Iron catalysts for selective anti-markovnikov alkene hydrosilylation using tertiary silanes. Science, 2012, 335: 567–570 Chen C, Hecht MB, Kavara A, et al. Rapid, regioconvergent, solvent-free alkene hydrosilylation with a cobalt catalyst. J Am Chem Soc, 2015, 137: 13244–13247 Bandari R, Buchmeiser MR. Polymeric monolith supported Ptnanoparticles as ligand-free catalysts for olefinhydrosilylation under batch and continuous conditions. Catal Sci Technol, 2012, 2: 220–226 Zhang D, Huo W, Wang J, et al. Synthesis of allyl-ended hyperbranched organic silicone resin by halloysite-supported platinum catalyst. J Appl Polym Sci, 2012, 126: 1580–1584 Zhang D, Wang J, Cheng X, et al. Synthesis of heterogeneous shape-controllable nano-hyperbranched polymer/Pt(0) catalyst with high catalytic activity in hydrosilylation. Macromol Res, 2012, 20: 549–551 Galeandro-Diamant T, Zanota ML, Sayah R, et al. Platinum nanoparticles in suspension are as efficient as Karstedt’s complex for alkene hydrosilylation. Chem Commun, 2015, 51: 16194–16196 Ciriminna R, Pandarus V, Gingras G, et al. Closing the organosilicon synthetic cycle: efficient heterogeneous hydrosilylation of alkenes over SiliaCat Pt(0). ACS Sustain Chem Eng, 2013, 1: 249–253 Corma A, González-Arellano C, Iglesias M, et al. Gold nanoparticles and gold(III) complexes as general and selective hydrosilylation catalysts. Angew Chem Int Ed, 2007, 46: 7820–7822 Pagliaro M, Ciriminna R, Pandarus V, et al. Platinum-based heterogeneously catalyzed hydrosilylation. Eur J Org Chem, 2013, 2013: 6227–6235 Newton MA. Dynamic adsorbate/reaction induced structural change of supported metal nanoparticles: heterogeneous catalysis and beyond. Chem Soc Rev, 2008, 37: 2644–2657 Walter MG, Warren EL, McKone JR, et al. Solar water splitting cells. Chem Rev, 2010, 110: 6446–6473 Bing Y, Liu H, Zhang L, et al. Nanostructured Pt-alloy electrocatalysts for PEM fuel cell oxygen reduction reaction. Chem Soc Rev, 2010, 39: 2184–2202 Daniel MC, Astruc D. Gold nanoparticles: assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology. Chem Rev, 2004, 104: 293–346 Stamenkovic VR, Fowler B, Mun BS, et al. Improved oxygen reduction activity on Pt3Ni(111) via increased surface site availability. Science, 2007, 315: 493–497 Wu Y, Cai S, Wang D, et al. Syntheses of water-soluble octahedral, truncated octahedral, and cubic Pt–Ni nanocrystals and their structure–activity study in model hydrogenation reactions. J Am Chem Soc, 2012, 134: 8975–8981 Cai S, Duan H, Rong H, et al. Highly active and selective catalysis of bimetallic Rh3Ni1 nanoparticles in the hydrogenation of nitroarenes. ACS Catal, 2013, 3: 608–612 Cui C, Gan L, Heggen M, et al. Compositional segregation in shaped Pt alloy nanoparticles and their structural behaviour during electrocatalysis. Nat Mater, 2013, 12: 765–771 Rong H, Cai S, Niu Z, et al. Composition-dependent catalytic activity of bimetallic nanocrystals: AgPd-catalyzed hydrodechlorination of 4-chlorophenol. ACS Catal, 2013, 3: 1560–1563 Chen C, Kang Y, Huo Z, et al. Highly crystalline multimetallic nanoframes with three-dimensional electrocatalytic surfaces. Science, 2014, 343: 1339–1343 Chen G, Zhao Y, Fu G, et al. Interfacial effects in iron-nickel hydroxide-platinum nanoparticles enhance catalytic oxidation. Science, 2014, 344: 495–499 Huang X, Zhao Z, Chen Y, et al. A rational design of carbonsupported dispersive Pt-based octahedra as efficient oxygen reduction reaction catalysts. Energy Environ Sci, 2014, 7: 2957–2962 Li Z, Yu R, Huang J, et al. Platinum–nickel frame within metalorganic framework fabricated in situ for hydrogen enrichment and molecular sieving. Nat Commun, 2015, 6: 8248–8256 Cui C, Gan L, Li HH, et al. Octahedral PtNi nanoparticle catalysts: exceptional oxygen reduction activity by tuning the alloy particle surface composition. Nano Lett, 2012, 12: 5885–5889