Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 59, Pages 13445-13450Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202001276
Keywords
alkynes; boron-ligand cooperation; density functional calculations; frustrated Lewis pair; hydrogenation
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Funding
- FCI
- DFG
- Projekt DEAL
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The metal-freecisselective hydrogenation of alkynes catalyzed by a boroxypyridine is reported. A variety of internal alkynes are hydrogenated at 80 degrees C under 5 bar H(2)with good yields and stereoselectivity. Furthermore, the catalyst described herein enables the first metal-free semihydrogenation of terminal alkynes. Mechanistic investigations, substantiated by DFT computations, reveal that the mode of action by which the boroxypyridine activates H(2)is reminiscent of the reactivity of an intramolecular frustrated Lewis pair. However, it is the change in the coordination mode of the boroxypyridine upon H(2)activation that allows the dissociation of the formed pyridone borane complex and subsequent hydroboration of an alkyne. This change in the coordination mode upon bond activation is described by the term boron-ligand cooperation.
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