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. 2019 Nov 18;58(47):16889-16893.
doi: 10.1002/anie.201910908. Epub 2019 Oct 11.

Pushing the Lewis Acidity Boundaries of Boron Compounds With Non-Planar Triarylboranes Derived from Triptycenes

Ali Ben Saida  1 , Aurélien Chardon  1 , Arnaud Osi  1 , Nikolay Tumanov  1 , Johan Wouters  1 , Abel I Adjieufack  1 , Benoît Champagne  1 , Guillaume Berionni  1
Affiliations

Pushing the Lewis Acidity Boundaries of Boron Compounds With Non-Planar Triarylboranes Derived from Triptycenes

Ali Ben Saida et al. Angew Chem Int Ed Engl. .

Abstract

Bending the planar trigonal boron center of triphenylborane by connecting its aryl rings with carbon or phosphorus linkers gave access to a series of 9-boratriptycene derivatives with unprecedented structures and reactivities. NMR spectroscopy and X-ray diffraction of the Lewis adducts of these non-planar boron Lewis acids with weak Lewis base revealed particularly strong covalent bond formation. The first Lewis adduct of a trivalent boron compounds with the Tf2 N- anion illustrates the unrivaled Lewis acidity of these species. Increasing the pyramidalization of the boron center and using a cationic phosphonium linker resulted in an exceptional enhancement of Lewis acidity. Introduction of a phosphorus and a boron atom at each edge of a triptycene framework, allowed access to new bifunctional Lewis acid-base 9-phospha-10-boratriptycenes featuring promising reactivity for the activation of carbon-halogen bonds.

Keywords: Lewis acids; Lewis superacid; boron; non-planar; triarylboranes.

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