Dihydrogen Activation by Antiaromatic Pentaarylboroles
Citations Over TimeTop 10% of 2010 papers
Abstract
Facile metal-free splitting of molecular hydrogen (H(2)) is crucial for the utilization of H(2) without the need for toxic transition-metal-based catalysts. Frustrated Lewis pairs (FLPs) are a new class of hydrogen activators wherein interactions with both a Lewis acid and a Lewis base heterolytically disrupt the hydrogen-hydrogen bond. Here we describe the activation of hydrogen exclusively by a boron-based Lewis acid, perfluoropentaphenylborole. This antiaromatic compound reacts extremely rapidly with H(2) in both solution and the solid state to yield boracyclopent-3-ene products resulting from addition of hydrogen atoms to the carbons alpha to boron in the starting borole. The disruption of antiaromaticity upon reaction of the borole with H(2) provides a significant thermodynamic driving force for this new metal-free hydrogen-splitting reaction.
Related Papers
- → Frustrated Lewis Pairs: Metal‐free Hydrogen Activation and More(2009)1,960 cited
- → Frustrated Lewis pairs: a new strategy to small molecule activation and hydrogenation catalysis(2009)566 cited
- → Heterolytic Cleavage of H2by Frustrated B/N Lewis Pairs(2011)67 cited
- → Recent Advances in Water-Tolerance in Frustrated Lewis Pair Chemistry(2018)51 cited
- → Heterogeneous Catalysis by Frustrated Lewis Pairs(2020)4 cited