[(acridine)BCl2]+: A borenium cation that is a strong boron- and carbon-based Lewis acid

Clark, Ewan R., Ingleson, Michael J. (2013) [(acridine)BCl2]+: A borenium cation that is a strong boron- and carbon-based Lewis acid. Organometallics, 32 (22). pp. 6712-6717. ISSN 0276-7333. (doi:10.1021/om400463r) (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided)

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http://www.dx.doi.org/10.1021/om400463r

Abstract

[(acridine)BCl2][AlCl4] was synthesized by halide abstraction from (acridine)BCl3 with AlCl3. The hydride ion affinity of the C9 position in [(acridine)BCl2]+ was calculated to be 14 kcal mol–1 greater than that at boron. [(acridine)BCl2][AlCl4] reacts with 1 equiv of acridine to form the strained boronium cation [(acridine)2BCl2][AlCl4] and with P(mesityl)3 by photoinduced one-electron transfer to form the 9,9?-biacridane moiety by radical coupling. A stable frustrated Lewis pair (FLP) was formed on combining [(acridine)BCl2][AlCl4] and 2,4,6-tri-tert-butylpyridine (TBP), which heterolytically activated H2 at 100 °C. The ultimate location of the hydride from H2 activation was the C9 position of acridine and not boron. Carbon Lewis acid based reactivity also occurred when thieno[3,2-b]thiophene was added to the [(acridine)BCl2][AlCl4]/TBP FLP or to [(acridine)2BCl2][AlCl4], with arylation of acridine at C9 observed for both.

Item Type: Article
DOI/Identification number: 10.1021/om400463r
Uncontrolled keywords: Arylations, Carbon-based, Frustrated lewis pairs, Halide abstraction, Lewis Acid, One-electron transfer, Photo-induced, Radical coupling, Carbon, Free radical reactions, Hydrides, Positive ions, Boron
Subjects: Q Science > QD Chemistry
Divisions: Faculties > Sciences > School of Physical Sciences > Functional Materials Group
Depositing User: Giles Tarver
Date Deposited: 29 Jul 2015 15:09 UTC
Last Modified: 29 May 2019 14:56 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/49872 (The current URI for this page, for reference purposes)
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