Synthesis of α-keto aldehydes via selective Cu(i)-catalyzed oxidation of α-hydroxy ketones

Abstract

An efficient approach to synthesize α-keto aldehydes was established through selective oxidation of α-hydroxy ketones catalyzed by Cu(I) using oxygen as oxidant. A wide array of α-keto aldehydes was prepared...

Synthesis of N-Substituted 3-Hydroxypyridinium Salts from Bioderived 5-Hydroxymethylfurfural in Water

“…As reported previously, 2,5-dioxohexanal (DOH) was synthesized from HMF via 1-hydroxy-2,5-hexanedione (HHD) as the intermediate through Ir-catalyzed hydrogenation followed by Cu(I)-catalyzed oxidation in 70% and 93% isolated yields, respectively. , It is worth noting that Fu and co-workers have reported the synthesis of HHD from HMF in 92% yield . With three carbonyl groups, DOH is recognized as a versatile bioderived scaffold for the syntheses of value-added chemicals.…”

“…The reactions of DOH and sec-alkylamine hydrochlorides under the optimized conditions did not form the desired products. However, they were formed when 1,4dioxane replaced H 2 O as the solvent (32,33,46). N-Hydroxy-3-hydroxypyridinium salt (31), an important precursor of pyridine N-oxide, was synthesized in 63% yield by reacting DOH with hydroxylamine hydrochloride in dioxane.…”

A New Strategy for the Synthesis of Valuable Benzenoid Aromatics from Bioderived 5-Hydroxymethylfurfural (HMF) under Mild Conditions

“…Following the procedures reported recently by our group, [44][45][46] DOH was synthesized from HMF via 1hydroxy-2,5-hexanedione (HHD) as intermediate through Ir catalyzed hydrogenation followed by Cu(I)catalyzed oxidation in 70% and 93% isolated yields respectively. It is worth to be noted that Fu and coworkers had already synthesized HHD from HMF in 98% yield.…”

Cu‐Catalyzed Tandem Oxidation‐Intramolecular Cannizzaro Reaction of Biorenewables and Bioactive Molecules

“…− The catalytic approaches remain limited to the use of Fe(OAc) 2/ TEMPO/O 2 [17] and Cu(OAc) 2 /O 2 , [22,23] and suffer from the need of very high catalyst loading. A recent report on the selective Cu(I)‐catalyzed oxidation of primary α ‐ketoalcohols using O 2 as a sole oxidant overcame these drawbacks [24] …”