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Tris(ortho-carboranyl)borane: An Isolable, Halogen-Free, Lewis Superacid
Manjur O Akram1, John R Tidwell1, Jason L Dutton2
1Department of Chemistry and Biochemistry, Baylor University, One Bear Place #97348, Waco, TX 76798, USA.
Abstract:
The synthesis of tris(ortho-carboranyl)borane (BoCb3 ), a single site neutral Lewis superacid, in one pot from commercially available materials is achieved. The high fluoride ion affinity (FIA) confirms its classification as a Lewis superacid and the Gutmann-Beckett method as well as adducts with Lewis bases indicate stronger Lewis acidity over the widely used fluorinated aryl boranes. The electron withdrawing effect of ortho-carborane and lack of pi-delocalization of the LUMO rationalize the unusually high Lewis acidity. Catalytic studies indicate that BoCb3 is a superior catalyst for promoting C-F bond functionalization reactions than tris(pentafluorophenyl)borane [B(C6 F5 )3 ].
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