Copper-catalyzed addition of diboron reagents to alpha,beta-acetylenic esters: efficient synthesis of beta-boryl-alpha,beta-ethylenic esters.
ABSTRACT The efficient copper-catalyzed addition reaction of bis(pinacolato)diboron to alpha,beta-acetylenic esters has been developed, which produces the corresponding beta-borylated-alpha,beta-ethylenic esters in high yields under mild reaction conditions.
- SourceAvailable from: Piet W N M van Leeuwen[show abstract] [hide abstract]
ABSTRACT: The reactivity of organotransition metal complexes is dependent on the ligand environment of the metal. This Account describes the development and application of new diphosphine ligands, designed to induce large P-M-P angles in transition metal complexes. Aided by computational chemistry, a homologous range of diphosphines based on rigid heterocyclic aromatic backbones of the xanthene-type with natural bite angles of approximately 100-134 degrees have been developed. The special structure of the ligands has an enormous impact on stability and reactivity of various transition metal complexes. Highly active and selective catalysts have been obtained by influencing this reactivity.Accounts of Chemical Research 12/2001; 34(11):895-904. · 20.83 Impact Factor
- Journal of the American Chemical Society 11/1973; 95(20):6837-8. · 10.68 Impact Factor
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ABSTRACT: [reaction: see text] The efficient addition of bis(pinacolato)diboron to alpha,beta-unsaturated carbonyl compounds with a copper-diphosphine catalyst has been carried out. A dramatic rate acceleration of the reaction was realized by adding alcohol additives. With use of this procedure, a variety of alpha,beta-unsaturated carbonyl compounds including conjugated substrates at the acid oxidation level such as esters and nitriles were reacted to give to the corresponding beta-boryl carbonyl compounds in high yields.Organic Letters 11/2006; 8(21):4887-9. · 6.14 Impact Factor