Transfer-hydrogenation reactions of ketones/aldehydes in water using first generation ruthenium indenylidene olefin metathesis catalyst: One step towards sequential cross-metathesis/transfer hydrogenation reactions

• Published in: Molecular catalysis Vol. 480; p. 110640
• Main Authors: Öztürk, Bengi Özgün, Öztürk, Sinem
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-01-2020
• Subjects: 10-undecenal; Aqueous media; Cross-metathesis; Emulsion; One-pot reaction; Ruthenium indenylidene; Transfer hydrogenation; Cross-metathesis; Transfer hydrogenation; 10-undecenal; Emulsion; Aqueous media; Ruthenium indenylidene; One-pot reaction
• ISSN: 2468-8231; 2468-8231
• DOI: 10.1016/j.mcat.2019.110640

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•One pot cross-metathesis/transfer hydrogenation (CM/TH) of 10-undecenal in water was investigated.•Ruthenium indenylidene catalyst (M1) was used in transfer hydrogenation reactions in water.•A conversion of 99% was obtained in transfer hydrogenation of acetophenone using 1% M1 in water.•Sequential CM/TH can even run under air atmosphere using tap water.
The transfer hydrogenation reactions of various ketones/aldehydes and one-pot cross-metathesis/transfer hydrogenation (CM/TH) reactions of 10-undecenal were carried out in water media using first generation ruthenium-indenylidene complex (M1). A stable emulsion with an average particle size of 23.00 (±7.20) nm was formed in water media using non-ionic (Tween 20) and cationic (dodecyltrimethylammonium chloride) surfactants in the presence of acetophenone, M1 (1%) and sodium formate, yielding corresponding alcohol derivatives in quantitative yields.
The performance of M1 (5%) was tested on sequential cross-metathesis/transfer hydrogenation reaction of 10-undecenal using methyl acrylate as the cross-metathesis partner in water. The sequential CM/TH reaction of 10-undecenal was found to proceed even in tap water under air atmosphere using micellar catalyst system, giving the corresponding CM/TH product in 65% yield.