Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 30, Pages 12402-12406Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202003119
Keywords
Lewis adducts; non-planar boron Lewis acids; triarylborane; triptycene
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Funding
- Fond National de la Recherche Scientifique (FNRS) [F.4513.18]
- FNRS-FRFC
- Walloon Region
- University of Namur [GEQ U.G006.15, U.G018.19, 1610468, RW/GEQ2016]
- University of Namur
- Namur Institute of Structured Matter (NISM)
- Fond National de la Recherche Scientifique (FRIA PhD grants)
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A highly bent triarylborane, 9-boratriptycene, was generated in solution by selective protodeboronation of the corresponding tetra-aryl boron ate complex with the strong Bronsted 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 pi donation from the triptycene aryl rings to the boron vacant p(z) orbital is one of the main reasons for its high Lewis acidity.
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