Controlled Generation of 9-Boratriptycene by Lewis Adduct Dissociation: Accessing a Non‐Planar Triarylborane

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Résumé

A highly bent triarylborane, 9-boratriptycene, was generated in solution by selective protodeboronation of the corresponding tetra-aryl boron ate complex with the strong Brønsted acid HNTf2. The iptycene core confers enhanced Lewis acidity to 9-boratriptycene, making it unique in terms of structure and reactivity. We studied the stereoelectronic properties of 9-boratriptycene by quantifying its association with small N- and O-centered Lewis bases, as well as with sterically hindered phosphines. The resultant Lewis adducts exhibited unique structural, spectroscopic, and photophysical properties. Beyond the high pyramidalization of the 9-boratriptycene scaffold and its low reorganization energy upon Lewis base coordination, quantum chemical calculations revealed that the absence of π donation from the triptycene aryl rings to the boron vacant pz orbital is one of the main reasons for its high Lewis acidity.

langue originaleAnglais
Numéro d'article10.1002/ange.202003119
Pages (de - à)12502-12506
Nombre de pages5
journalAngewandte Chemie
Volume132
Numéro de publication30
Les DOIs
Etat de la publicationPublié - 20 juil. 2020

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