• Title of article

    Structure of a push–pull olefin prepared by ynamine hydro­boration with a borandiol ester

  • Author/Authors

    Gubler, Joël Laboratorium für Organische Chemie - ETH Zürich, Zürich, Switzerland , Chen, Peter Laboratorium für Organische Chemie - ETH Zürich, Zürich, Switzerland

  • Pages
    14
  • From page
    1
  • To page
    14
  • Abstract
    N-[(Z)-2-(2H-1,3,2-Benzodioxaborol-2-yl)-2-phenyl­ethen­yl]-N-(propan-2-yl)aniline, C23H22BNO2, contains a C=C bond that is conjugated with a donor and an acceptor group. An analysis that included similar push–pull olefins revealed that bond lengths in their B—C=C—N core units correlate with the perceived acceptor and donor strength of the groups. The two phenyl groups in the mol­ecule are rotated with respect to the plane that contains the BCCN atoms, and are close enough for significant π-stacking. Definite characterization of the title compound demonstrates, for the first time in a reliable way, that hydro­boration of ynamines with borandiol esters is feasible. Compared to olefin hydro­boration with borane, the ynamine substrate is activated enough to undergo reaction with the less active hydro­boration reagent catecholborane.
  • Keywords
    crystal structure , hydro­boration , ynamine , push–pull olefin
  • Journal title
    Acta Crystallographica Section E: Crystallographic Communications
  • Serial Year
    2020
  • Record number

    2624069