Regioselective C–H hydroxylation of n-alkanes using Shilov-type Pt catalysis in perfluorinated micro-emulsions. Issue 5 (29th January 2020)

• Record Type: Journal Article
• Authors: Janssen, Michiel; De Vos, Dirk E.
• Is Part Of: Catalysis science & technology. Volume 10:Issue 5(2020)
• Page Start: 1264
• Page End: 1272
• Publication Date: 2020-01-29
• Subjects: Catalysis -- Periodicals; 541.395
• DOI: 10.1039/c9cy02320h
• Languages: English
• ISSNs: 2044-4753

Abstract

Abstract : In this work, the potential of combining Shilov-type Pt II and micellar catalysis to realize the challenging terminal C–H hydroxylation of saturated n -alkanes using water as the reaction medium is demonstrated. Abstract : Shilov-chemistry inspired catalysis has remained largely overlooked as a tool for establishing the remote hydroxylation of non-polar compounds, such as long linear alkanes, due to the need for an acidic aqueous solution. To circumvent the solubility issue, the concept of micellar catalysis is introduced, using Pt II in perfluorinated micro-emulsions. Notably, the terminal C–H activation of n -heptane is demonstrated under an oxygen atmosphere using perfluorooctanoic acid (PFOA) as a surfactant, along with the intrinsic ability of Pt II to convert the highly inert primary C–H bonds. Coordination of Pt II to the carboxylate groups of PFOA proved to be particularly important for achieving maximum catalyst activity towards the hydrocarbon substrate solubilized inside the micelle interior. Based on these insights, optimization of the reaction parameters allowed a positional selectivity of 60% for 1-heptanol, among the C7 alcohols, to be achieved, using low catalyst and surfactant loadings under acid-free conditions.