155956-32-4Relevant academic research and scientific papers
Combining high pressure and catalysis: Pinacol- or catecholborane hydroboration of functionalized olefins
Colin, Sylvie,Vaysse-Ludot, Lucile,Lecouve, Jean-Pierre,Maddaluno, Jacques
, p. 4505 - 4511 (2008/10/08)
The hydroboration of three families of functionalized olefins (1-bromo- and 1,3-dibromopropenes, allylamines, 2,3-dihydrofuran) by pinacolborane and catecholborane has been studied under various experimental conditions. For 1-bromo- and 1,3-dibromopropenes, pinacolborane (PBH) is a poor reagent that requires the use of high pressure in ethereal solvents and provides only by-products, resulting from the undesired β-bromoboronate regioisomer. By contrast, catecholborane (CBH) affords mainly the expected α-bromoboronate at atmospheric pressure. With dibenzylallylamine, PBH yields a mixture of the two possible regioisomers (β- and γ-amino-boronates), whatever the pressure, while CBH affords selectively the expected γ-isomer in good yields under atmospheric thermal conditions. For 2,3-dihydrofuran, only PBH gives an efficient access, in THF, to a mixture of the corresponding α- and β-regioisomers when combining the effects of 0.5% Wilkinson's catalyst and high pressure.
Combining high pressure and catalysis: Pinacol- or catecholborane hydroboration of functionalized olefins
Colin, Sylvie,Vaysse-Ludot, Lucile,Lecouve, Jean-Pierre,Maddaluno, Jacques
, p. 4505 - 4511 (2007/10/03)
The hydroboration of three families of functionalized olefins (1-bromo- and 1,3-dibromopropenes, allylamines, 2,3-dihydrofuran) by pinacolborane and catecholborane has been studied under various experimental conditions. For 1-bromo- and 1,3-dibromopropenes, pinacolborane (PBH) is a poor reagent that requires the use of high pressure in ethereal solvents and provides only by-products, resulting from the undesired β-bromoboronate regioisomer. By contrast, catecholborane (CBH) affords mainly the expected α-bromoboronate at atmospheric pressure. With dibenzylallylamine, PBH yields a mixture of the two possible regioisomers (β- and γ-aminoboronates), whatever the pressure, while CBH affords selectively the expected γ-isomer in good yields under atmospheric thermal conditions. For 2,3-dihydrofuran, only PBH gives an efficient access, in THF, to a mixture of the corresponding α- and β-regioisomers when combining the effects of 0.5% Wilkinson's catalyst and high pressure. The Royal Society of Chemistry 2000.
