Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 744, Issue -, Pages 149-155Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2013.06.005
Keywords
Frustrated Lewis pair; Phosphorus; Boron; Molecule activation; 1,2-Addition reaction
Categories
Funding
- Deutsche Forschungsgemeinschaft
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[Bis(pentafluorophenyl)phosphanyl]phenylacetylene (4) undergoes a regioselective hydroboration reaction with HB(C6F5)(2) to yield the geminal frustrated Lewis pair 5 that bears pairs of strongly electron-withdrawing C6F5 substituents at both boron and phosphorus. The X-ray crystal structure analysis has revealed that there is no direct P-B interaction in 5. This has been confirmed by both solid state and solution NMR spectroscopy. The non-interacting geminal FLP 5 undergoes 1,2-P/B addition reactions to carbonyl compounds (benzaldehyde, trans-cinnamic aldehyde), to the C=N bond of phenylisocyanate and to the C C triple bonds of several alkynes (1-pentyne, phenylacetylene, 4-octyne). The frustrated Lewis pair 5 and several reaction products were characterized by X-ray diffraction. (C) 2013 Elsevier B.V. All rights reserved.
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