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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Abstract
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.
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