Borenium Ion Catalyzed Hydroboration of Alkenes with N-Heterocyclic Carbene-Boranes

…, L Li, H Bonin, E Lacôte, DP Curran…

Index: Prokofjevs, Aleksandrs; Boussonniere, Anne; Li, Linfeng; Bonin, Helene; Lacote, Emmanuel; Curran, Dennis P.; Vedejs, Edwin Journal of the American Chemical Society, 2012 , vol. 134, # 29 p. 12281 - 12288

Full Text: HTML

Citation Number: 61

Abstract

Treatment of alkenes such as 3-hexene, 3-octene, and 1-cyclohexyl-1-butene with the N- heterocyclic carbene (NHC)-derived borane 2 and catalytic HNTf2 (Tf= trifluoromethanesulfonyl (CF3SO2)) effects hydroboration at room temperature. With 3- hexene, surprisingly facile migration of the boron atom from C (3) of the hexyl group to C (2) was observed over a time scale of minutes to hours. Oxidative workup gave a mixture of ...