Orthogonal reactivity in boryl-substituted organotrifluoroborates.
A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Sandrock
Deidre L
DL
D001881:Borates / Q000737:chemistry*; D003432:Cross-Linking Reagents; D017611:Fluorine Compounds / Q000737:chemistry*; D006838:Hydrocarbons / Q000737:chemistry; D015394:Molecular Structure
D001881:Borates; D003432:Cross-Linking Reagents; D017611:Fluorine Compounds; D006838:Hydrocarbons