Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 52, Pages 15897-15900Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201507883
Keywords
chlorocarbamoylation; cyclization; homogenous catalysis; palladium; phosphaadamantane
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Funding
- Alphora Inc.
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- University of Toronto (U of T)
- Canada Council for the Arts
- NSERC
- RWTH Aachen
- MIWF NRW
- Evonik foundation
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Pharmaceutically relevant methylene oxindoles are synthesized by a palladium(0)-catalyzed intramolecular chlorocarbamoylation reaction of alkynes. A relatively under-explored class of caged phosphine ligands is uniquely suited for this transformation, enabling high levels of reactivity and exquisite trans selectivity. This report entails the first transition-metal-catalyzed atom-economic addition of a carbamoyl chloride across an alkyne.
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