1182710-75-3Relevant articles and documents
Copper-catalyzed highly regio- and stereoselective directed hydroboration of unsymmetrical internal alkynes: Controlling regioselectivity by choice of catalytic species
Semba, Kazuhiko,Fujihara, Tetsuaki,Terao, Jun,Tsuji, Yasushi
supporting information; experimental part, p. 4179 - 4184 (2012/05/31)
A highly selective synthesis of the αand β products by copper-catalyzed hydroboration utilizing two different catalytic copper species generated from pinacolborane (HBpin) and B2pin2 is reported. Regioselectivity in the crude reaction mixtures is found to be high, and the corresponding a products were isolated in good yields. In the case of an alkyne containing an alkenyl moiety, the regioselectivity decreased to 72:28. In hydroboration reactions catalyzed by other transition metals, selecting between hydrometalation and boryl metalation is difficult because the oxidative addition of HB to a metal center provides an H-M-B species, containing both H-M and B-M bonds. The α and β products are valuable intermediates used in the Suzuki-Miyaura cross-coupling reaction to regioselectively prepare various trisubstituted alkenes of types 5α and 5β.
