Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 696, Issue 1, Pages 170-178Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2010.08.034
Keywords
Addition reaction; Bimetallic catalysis; Z-Enamide; Hydroamidation; Lewis acid; Ruthenium
Categories
Funding
- Deutsche Forschungsgemeinschaft
- NanoKat
- Landesgraduiertenforderung Rheinland-Pfalz
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A catalyst system formed in situ from bis(2-methallyl)cycloocta-1,5-diene-ruthenium(II) [(cod)Ru(met)(2)], 1,4-bis(dicyclohexylphosphino)butane (dcypb) and ytterbium(III) triflate hydrate (Yb(OTf)(3)) was found to catalyze the addition of nitrogen nucleophiles to terminal alkynes under mild conditions to stereoselectively form the Z-enamide or Z-enimide products. Various secondary amides and imides could be added across the triple bond of a range of aliphatic and aromatic alkynes. The new bimetallic catalyst system sets new standards with regard to scope and selectivity for the synthesis of Z-configured anti-Markovnikov enamides. (C) 2010 Elsevier B.V. All rights reserved.
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