Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 50, Pages 16520-16524Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809112
Keywords
allylic compounds; heterogeneous catalysis; hydrazones; palladium; synthetic methods
Categories
Funding
- Canada Research Chair Foundation
- CFI
- FQRNT Center for Green Chemistry and Catalysis
- McGill University
- Shanghai Institute of Organic Chemistry (SIOC)
- NSERC
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Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.
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