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Tris(ortho-carboranyl)borane: An Isolable, Halogen-Free, Lewis Superacid

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posted on 2023-07-11, 02:26 authored by MO Akram, JR Tidwell, Jason DuttonJason Dutton, CD Martin
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(C6F5)3].

Funding

Baylor University, the Welch Foundation (Grant No. AA-1846), the National Science Foundation (Award No. 1753025), and the Australian Research Council (FT16010007, DP20010013).

History

Publication Date

2022-11-14

Journal

Angewandte Chemie - International Edition

Volume

61

Issue

46

Article Number

e202212073

Pagination

7p.

Publisher

Wiley

ISSN

1433-7851

Rights Statement

© 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.

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