Clean and Selective Catalytic C-H alkylation of Alkenes with Environmental friendly Alcohols
dc.contributor.author | Poater, Albert | |
dc.contributor.author | Vummaleti, Sai V. C. | |
dc.contributor.author | Polo, Alfonso | |
dc.contributor.author | Cavallo, Luigi | |
dc.date.accessioned | 2016-12-13T13:46:38Z | |
dc.date.available | 2016-12-13T13:46:38Z | |
dc.date.issued | 2016-09-14 | |
dc.identifier.citation | Poater A, Vummaleti SVC, Polo A, Cavallo L (2016) Clean and Selective Catalytic C-H alkylation of Alkenes with Environmental friendly Alcohols. Journal of Molecular Catalysis A: Chemical. Available: http://dx.doi.org/10.1016/j.molcata.2016.09.010. | |
dc.identifier.issn | 1381-1169 | |
dc.identifier.doi | 10.1016/j.molcata.2016.09.010 | |
dc.identifier.uri | http://hdl.handle.net/10754/622012 | |
dc.description.abstract | Bearing the alkylation of alkene substrates using alcohol as solvent, catalysed by the cationic Ru-based catalyst [(C6H6)(PCy3)(CO)RuH]+, DFT calculations have been carried out to get mechanistic insights of such an environmental friendly reaction. Hard experimental conditions of Yi and coworkers [Science2011, 333, 1613] allow the formation of a C-C bond between indene and ethanol. The predicted mechanism suggests a cationic Ru-alkenyl species once two equivalents of indene interact releasing a molecule of indane subproduct. Then, oxidative addition of the Csingle bondO bond of alcohol to Ru-alkenyl species leads to Ru-alkenyl-alkyl species, followed by the reductive elimination process produces the desired alkylation product and a Ru-hydroxo complex. Finally, vinylic Csingle bondH activation and water elimination regenerates the Ru-alkenyl species. In this paper we present a full description of the complete reaction pathway along with possible alternative pathways, which are predicted to display higher upper barriers. Furthermore, the present study explains the possible reasons for the absence of undesired products such as indene dimer or hydroxylated indene in the experiments. | |
dc.description.sponsorship | We thank the helpful comments of the referees that have improved this manuscript. We thank King Abdullah University of Science and Technology (CFF project) for support. A.P. thanks the Spanish MINECO for a project CTQ2014-59832-JIN. | |
dc.publisher | Elsevier BV | |
dc.relation.url | http://www.sciencedirect.com/science/article/pii/S138111691630382X | |
dc.rights | NOTICE: this is the author’s version of a work that was accepted for publication in Journal of Molecular Catalysis A: Chemical. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Journal of Molecular Catalysis A: Chemical, 13 September 2016. DOI: 10.1016/j.molcata.2016.09.010 | |
dc.subject | homogeneous catalysis | |
dc.subject | ruthenium catalysis | |
dc.subject | DFT calculations | |
dc.subject | green chemistry | |
dc.subject | alkene | |
dc.subject | C-H alkylation | |
dc.title | Clean and Selective Catalytic C-H alkylation of Alkenes with Environmental friendly Alcohols | |
dc.type | Article | |
dc.contributor.department | Chemical Science Program | |
dc.contributor.department | KAUST Catalysis Center (KCC) | |
dc.contributor.department | Physical Science and Engineering (PSE) Division | |
dc.identifier.journal | Molecular Catalysis | |
dc.eprint.version | Post-print | |
dc.contributor.institution | Institut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, Campus Montilivi, 17003 Girona, Catalonia, Spain | |
kaust.person | Vummaleti, Sai V. C. | |
kaust.person | Cavallo, Luigi | |
dc.date.published-online | 2016-09-14 | |
dc.date.published-print | 2017-07 |
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