Ruthenium Nanoparticles Supported on Hydroxyapatite as an Efficient and Recyclable Catalyst for cis‐Dihydroxylation and Oxidative Cleavage of Alkenes

Abstract

Impregnation of hydroxyapatite with colloidal ruthenium results in the formation of a catalyst that effects cis‐dihydroxylation and oxidative cleavage of alkenes to their respective cis‐1,2‐diols and carbonyl products in good to excellent yields (see scheme). The supported ruthenium catalyst can be easily recycled and reused for consecutive reaction runs without significant deterioration of the catalytic activities. R1, R2=H, alkyl, aryl.

A new glance at ruthenium sorption mechanism on hydroxy, carbonate, and fluor apatites: Analytical and structural studies

“…In this way, Ru 3+ -containing hydroxy apatite (HAp) was found to be an effective and selective catalyst for several oxidative reactions: diels-alder, aldol reactions, and the racemization of configurationally stable chiral secondary alcohols. By comparison with other supported Ru catalysts, this modified apatite presents several advantages, e.g., simple usage, no leaching of Ru into the reaction media, and easy recovery of the catalyst after the reaction by simple filtration [2][3][4][5][6][7][8][9][10][11].…”

Recent Developments in Metal‐Catalyzed Dihydroxylation of Alkenes

“…Immobilization of ruthenium catalyst for dihydroxylation of alkenes was demonstrated by Yu and Che [63]. A colloidal ruthenium species was suspended with calcium hydroxyapatite in water in their grafting process.…”

Polymer Supported Vanadium Complexes as Catalysts for the Oxidation of Alkenes in Water

“…The typical reagents for this transformation adopted in most textbooks include ozone and some metal oxides such as OsO 4 and RuO 4 in combination with a co-oxidant [1][2][3][4][5][6][7][8], but the major drawback for these processes is the concern of chemical wastes and for safety. Thus, the search for alternative catalytic systems for bishydroxylation and/or oxidative cleavage of C=C has received considerable attention particularly with the use of ruthenium or vanadium-based catalysts [7][8][9]. However, development of efficient and green protocols for this oxidation is an area of growing interest due to the environmental concerns [5][6][7][8][9].…”

“…Thus, the search for alternative catalytic systems for bishydroxylation and/or oxidative cleavage of C=C has received considerable attention particularly with the use of ruthenium or vanadium-based catalysts [7][8][9]. However, development of efficient and green protocols for this oxidation is an area of growing interest due to the environmental concerns [5][6][7][8][9]. A combination of Na 2 WO 4 and H 2 O 2 does provide a good catalytic system for the oxidation of alkenes [10,11].…”