American Chemical Society
om500128a_si_001.pdf (1.32 MB)

Tris(5,6,7,8-tetrafluoronaphthalen-2-yl)borane, a Partially Fluorinated Boron Lewis Acid with Fluorination Distal to the Boron Atom

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journal contribution
posted on 2014-03-10, 00:00 authored by Jens Mohr, Mustafa Durmaz, Elisabeth Irran, Martin Oestreich
Typical congeners of the boron Lewis acid tris­(pentafluorophenyl)­borane, B­(C6F5)3, are fluorinated at the aryl groups directly attached to the boron atom. The chemistry of related electron-deficient boranes with fluorination distal to the Lewis acidic center is largely unexplored. The preparation and characterization of tris­(5,6,7,8-tetrafluoronaphthalen-2-yl)­borane are reported. It serves as a model system that provides sites for further substitution at C-1 and C-3 of the naphthalen-2-yl units. A Gutmann–Beckett analysis of its Lewis acidity revealed that, despite remote fluorination, it is as Lewis acidic as B­(C6F5)3. The new Lewis acid performs equally well in CO and CN reduction as well as dehydrogenative Si–O coupling involving Si–H bond activation. Adducts with water and a phosphine oxide are crystallographically characterized.