Clean and Selective Catalytic C-H alkylation of Alkenes with Environmental friendly Alcohols

Albert Poater, Sai V. C. Vummaleti, Alfonso Polo, Luigi Cavallo

Research output: Contribution to journalArticlepeer-review

4 Scopus citations


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.
Original languageEnglish (US)
Pages (from-to)69-75
Number of pages7
JournalJournal of Molecular Catalysis A: Chemical
StatePublished - Sep 14 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.


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