A Highly Efficient Catalyst for Selective Oxidative Scission of Olefins to Aldehydes: Abnormal-NHC–Ru(II) Complex in Oxidation Chemistry

Abstract

The utility and selectivity of the catalyst [Ru(COD)(L(1))Br2] (1) bearing a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based abnormal N-heterocyclic carbene ligand L(1) is demonstrated toward selective oxidation of C═C bonds to aldehydes and C≡C bonds to α-diketones in an EtOAc/CH3CN/H2O solvent mixture at room temperature using a wide range of substrates, including highly functionalized sugar- and amino acid-derived compounds.

cis-Oxoruthenium complexes supported by chiral tetradentate amine (N4) ligands for hydrocarbon oxidations

“…The timespan of the reaction (1 h) is comparable to that (30 min) reported by Bera and co-workers using an abnormal-NHC–Ru( ii ) catalyst. 75 …”

Donor‐Flexible Bis(pyridylidene amide) Ligands for Highly Efficient Ruthenium‐Catalyzed Olefin Oxidation

“…The most established catalytic system is the osmium‐based Lemieux–Johnson catalyst, as well as variations thereof based on osmium as well as ruthenium, which generally require high catalyst loading and tend to suffer from rapid overoxidation to produce the acid predominantly . Recently, Bera and co‐workers pioneered a more efficient system based on an abnormal carbene for the oxidation of C=C bonds into C=O functional groups at ambient temperature with high selectivity . Preliminary mechanistic insight suggests a catalytic cycle involving toggling between a low‐valent Ru II intermediate and a high‐valent Ru IV (=O) 2 species.…”

Selective oxidative cleavage of terminal olefins into aldehydes catalyzed by copper(ii) complex

“…[4][5][6] At present, the oxidation of olefins into aldehydes is one of the bottlenecks and challenging problems in synthetic chemistry and petrochemical industry. Although some studies on oxidative cleavage of olefins into aldehydes through Fe, [7][8][9][10][11] Pd, [12][13] Ru, [14][15][16] Os, [17][18] Au 19 catalysts, biphasic PEG-300/scCO 2 catalyst 20 and supported catalysts [21][22][23] with sodium periodate or other oxidants have been reported, the problems of low activity, low selectivity, environment unfriendly and severe reaction conditions are still not resolved. [24][25] In recent years, the development of a simple and effective, environmentally benign oxidation methods is attracting growing interest, 26 with protocols based on cheap and abundant metal catalysts in combination with clean oxidants being highly sought.…”