An efficient palladium-catalyzed synthesis of benzils from aryl bromides: vinylene carbonate as a synthetic equivalent of glyoxal

• Published in: Tetrahedron letters Vol. 52; no. 27; pp. 3463 - 3466
• Main Authors: Kim, Ko Hoon, Park, Bo Ram, Lim, Jin Woo, Kim, Jae Nyoung
• Format: Journal Article
• Language: English
• Published: Kidlington Elsevier Ltd 06-07-2011; Elsevier
• Subjects: Aerobic oxidation; Aromatic compounds; Benzil; Benzils; Benzoin; Bromides; Carbonates; Chemistry; Derivatives; Equivalence; Exact sciences and technology; Glyoxal; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Kinetics and mechanisms; Organic chemistry; Palladium; Preparations and properties; Reactivity and mechanisms; Tetrahedrons; Vinylene carbonate; Vinylene carbonate; Benzils; Palladium; Glyoxal; Aerobic oxidation; Cesium carbonate; One pot reaction; Arylation; Catalytic reaction; Organic carbonate; Palladium complex; Transition metal; Aerobe; Diketone; Oxygen heterocycle; Ring cleavage; Reaction mechanism; Benzenic compound; Oxidation; Chemical synthesis; Platinoid
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.04.108

An expedient synthetic procedure of benzil derivatives from aryl bromides was developed using vinylene carbonate as a glyoxal equivalent in a palladium-catalyzed reaction. The reaction involved a sequential diarylation of vinylene carbonate to form 4,5-diaryl-1,3-dioxol-2-one, ring-opening to benzoin derivative, and an oxidation process.