THEORETICAL EXPLANATION FOR CATALYTIC HYDROSILYLATION OF SOME ORGANIC MOLECULES MEDIATED BY A PHOSPHORUS DICATION COMPOUND

Yıl 2021, , 30 - 36, 30.08.2021

Cem Burak Yıldız

https://doi.org/10.20290/estubtdb.898776

Öz

Catalysis reactions under metal-free and ambient conditions have received great interest in terms of economic and environmental issues. Especially, the applications of Lewis acids for the processes are having special interest due to their unique roles in a huge number of organic reactions. In this sense, a recent compound PIII dication has played an important role in the catalytic hydrosilylation of carbonyls and olefins. Herein theoretical calculations were carried out to elucidate the mechanisms of the experimentally reported and unknown reactions. The proposed mechanisms show that the reactions of a-d can occur spontaneously, whereas the formation of pyridine has endergonic nature.

Anahtar Kelimeler

DFT, catalysis, Phosphorus, Reaction mechanism

Destekleyen Kurum

Aksaray University coordinatorship of scientific research projects

Kaynakça

• [1] Sereda O, Tabassum S, Wilhelm R. Asymmetric Organocatalysis. Berlin, Heidelberg, Germany: Springer Berlin Heidelberg, 2009.
• [2] Dagorne S, Wehmschulte R. Recent developments on the use of group 13 metal complexes in catalysis. Chem Cat Chem, 2018; 10: 2509-2520.
• [3] Shen Q, Huang YG, Liu C, Xiao JC, Chen QY, Guo Y. Review of recent advances in C-F bond activation of aliphatic fluorides. J Fluor Chem, 2015; 179: 14–22. doi: 10.1016/j.jfluchem.2015.07.007
• [4] Douvris C, Nagaraja CM, Chen CH, Foxman BM, Ozerov OV. Hydrodefluorination and other hydrodehalogenation of aliphatic carbon-halogen bonds using silylium catalysis. J Am Chem Soc, 2010; 132: 4946–4953.
• [5] Douvris C, Ozerov OV. Hydrodefluorination of perfluoroalkyl groups using silylium-carborane catalysts. Science, 2008; 321, 1188-1190.
• [6] Stahl T, Klare HFT, Oestreich M. Main-group lewis acids for C–F bond activation. ACS Cat, 2013; 3: 1578–1587.
• [7] Ahrens M, Scholz G, Braun T, Kemnitz E. Catalytic hydrodefluorination of fluoromethanes at room temperature by silylium-ion-like surface species. Angew Chem Int Ed, 2013; 52: 5328–5332.
• [8] Pan B, Gabbai FP. [Sb(C6F5)4][B(C6F5)4]: An air stable, lewis acidic stibonium salt that activates strong element-fluorine bonds. J Am Chem Soc, 2014; 136: 9564–9567.
• [9] Farrell JM, Hatnean JA, Stephan DA. Activation of hydrogen and hydrogenation catalysis by a borenium cation. J Am Chem Soc, 2012; 134: 15728–15731.
• [10] Terada M, Kouchi M. Novel metal-free Lewis acid catalysis by phosphonium salts through hypervalent interaction. Tetrahedron, 2006; 62: 401–409.
• [11] Caputo CB, Hounjet LJ, Dobrovetsky R, Stephan DW. Lewis acidity of organofluorophosphonium salts: Hydrodefluorination by a saturated acceptor. Science, 2013; 341: 1374–1377.
• [12] Zhu J, Perez M, Caputo CB, Stephan DW. Use of trifluoromethyl groups for catalytic benzylation and alkylation with subsequent hydrodefluorination. Angew Chem Int Ed, 2016; 55: 1417–1421.
• [13] Bayne JM, Stephan DW. Phosphorus lewis acids: emerging reactivity and applications in catalysis. Chem Soc Rev, 2016; 45; 765–774.
• [14] Fan YC, Kwon O. Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs. Chem Commun, 2013; 49: 11588–11619.
• [15] Burford N, Ragogna P. New synthetic opportunities using Lewis acidic phosphines. J Chem Soc Dalton Trans 2002; 4307–4315.
• [16] Gudat D. A very peculiar family of N-heterocyclic phosphines: unusual structures and the unique reactivity of 1,3,2-diazaphospholenes. Dalton Trans, 2016; 45; 5896–5907.
• [17] Slattery JM, Hussein S. How Lewis acidic is your cation? Putting phosphenium ions on the fluoride ion affinity scale. Dalton Trans, 2012; 41: 1808–1815.
• [18] Dorevic N, Tay MQY, Muthaiah S, Ganguly R, Dimic D. C–F bond activation by transient phosphenium dications. Inorg Chem, 2015; 54: 4180–4182.
• [19] Dorevic N, Ganguly R, Petkovic M, Vidovic D. E–H (E = B, Si, C) Bond activation by tuning structural and electronic properties of phosphenium cations. Inorg Chem, 2017; 56: 14671–14681.
• [20] Chitnis SS, Krischer F, Stephan DW. Catalytic hydrodefluorination of C-F bonds by an air-stable PIII lewis acid. Chem Eur J, 2018; 24: 6543-6546.
• [21] Chitnis SS, LaFortune JHW, Cummings H, Liu LL, Andrews R, Stephan DW. Phosphorus coordination chemistry in catalysis: Air stable P(III)-dications as lewis acid catalysts for the allylation of C-F bonds. Organomet, 2018; 37: 4540-4544.
• [22] Andrews RJ, Chitnis SS, Stephan DW. Carbonyl and olefin hydrosilylation mediated by an air-stable phosphorus(III) dication under mild conditions. Chem Commun, 2019; 55: 5599-5602.
• [23] Pérez M, Hounjet LJ, Caputo CB, Dobrovetsky R, Stephan DW. Olefin isomerization and hydrosilylation catalysis by lewis acidic organofluorophosphonium salts. J Am Chem Soc, 2013; 135; 18308–18310.
• [24] Pérez M, Qu ZW, Caputo CB, Podgorny V, Hounjet LJ, Hansen A, Dobrovetsky R, Grimme S, Stephan DW. Hydrosilylation of ketones, imines and nitriles catalysed by electrophilic phosphonium cations: Functional group selectivity and mechanistic considerations. Chem Eur J, 2015; 21; 6491–6500.
• [25] Vom Stein T, Perez M, Dobrovetsky R, Winkelhaus D, Caputo CB, Stephan DW. Electrophilic fluorophosphonium cations in frustrated Lewis pair hydrogen activation and catalytic hydrogenation of olefins. Angew Chem Int Ed, 2015; 54: 10178–10182.
• [26] Kostenko A, Dobrovetsky R. The role of the fluoro–hydrido–phosphorane intermediate in catalytic hydrosilylation of acetophenone: Computational study. Eur J Org Chem, 2019; 318–322.
• [27] Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson, GA, Nakatsuji, H, Li X, et al. Gaussian 16, Revision B.01, Gaussian Inc: Wallingford CT., 2016. [28] Lee C, Yang W, Parr RG. Development of the colle-salvetti correlation-energy formula into a functional of the electron density. Phys Rev B, 1988; 37: 785-789.
• [29] Weigend F, Ahlrichs R. 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, 2005; 7: 3297-305.
• [30] Grimme S, Ehrlich S, Goerigk L. Effect of the damping function in dispersion corrected density functional theory. J Comp Chem, 2011; 32: 1456-1465.
• [31] Gonzalez C, Schlegel HB. Improved algorithms for reaction path following: higher‐order implicit algorithms. J Chem Phys, 1991; 95: 5853-5860.
• [32] Wiberg KB. Application of the pople–santry–segal CNDO method to the cyclopropylcarbinyl and cyclobutyl cation and to bicyclobutane. Tetrahedron, 1968; 24: 1083-1096.
• [33] Dennington RII, Keith T, Millam J, Eppinnett K, Hovell WL, Gilliland R. GaussView v.5.0.9 Visualizer and Builder. Gaussian Inc. Wallingford CT., 2009.