N D Zelinsky Institute of Organic Chemistry-RAS, Russia
Title: Oxidative cross-dehydrogenative coupling with C-O bond formation
Biography: Alexander O Terent’ev
Oxidative cross-dehydrogenative coupling is included in the modern trends of organic chemistry. It eliminates necessity for introduction of additional functional groups and affords direct coupling in one stage (via selective C-H activation) with limited amount of wastes, high atom- and step- economy. Oxidative cross-dehydrogenative C-C coupling was studied in most detail; the C-N, C-P, and C-O cross-coupling reactions are less developed. The problem is in achieving of high selectivity in the cross-dehydrogenative C-O coupling because the starting compounds are prone to side oxidation and fragmentation reactions producing, for example, alcohols and carbonyl compounds. This gives rise to a problem of searching for oxidizing agents and reaction conditions suitable for the cross-coupling of different types of substrates. We discovered oxidative cross-dehydrogenative C-O coupling of 1, 3-dicarbonyl compounds, their heteroanalogs, and heterocycles with peroxides, oximes and hydroxyamides. The best results were obtained with the use of the widely available copper, iron, manganese or lanthanide salts as catalysts or oxidants.