Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 42, Pages 13122-13125Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201706893
Keywords
carbanions; carboxylic acids; dehydrogenation; palladium; synthetic methods
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Funding
- Yale University
- Nalas Engineering
- Sloan Foundation
- National Science Foundation (CAREER) [1653793]
- Rudolph J. Anderson postdoctoral fellowship
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1653793] Funding Source: National Science Foundation
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A highly practical and step-economic alpha,beta-dehydrogenation of carboxylic acids via enediolates is reported through the use of allyl-palladium catalysis. Dianions underwent smooth dehydrogenation when generated using Zn(TMP)(2)center dot 2LiCl as a base in the presence of excess ZnCl2, thus avoiding the typical decarboxylation pathway of these substrates. Direct access to 2-enoic acids allows derivatization by numerous approaches.
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