Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 54, Pages 12507-12511Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903229
Keywords
hydrofunctionalisation; hydrosilylation; metal-free synthesis; phosphorus; triphosphabenzene
Categories
Funding
- EPSRC [EP/G036764/1]
- University of Bristol
- NSERC Canada
- Canada Research Chair
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The aromatic heterocycle 2,4,6-tri-tert-butyl-1,3,5-triphosphabenzene reacts with a series of silanes, germanes and stannanes, with weaker E-H bonds reacting in an increasingly facile manner. All react by 1,4-addition to give bicyclic products with diastereomeric ratios varying with the substrate. Density functional theory (DFT) calculations show that activation of the E-H bond occurs across the 1,4-C/P axis of the triphosphabenzene, with the small energetic differences with respect to the stereochemistry of the addition offering insight into the experimentally observed diastereomeric ratios.
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