期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 11, 页码 4544-4549出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201915218
关键词
alkylation; allylic alcohols; carbanions; relay reactions; ruthenium
资金
- Canada Research Chair Foundation
- CFI
- FRQNT Center for Green Chemistry and Catalysis
- NSERC
- Killam Research Fellowship
- McGill University
- China Scholarship Council
Herein, we report a ruthenium-catalyzed redox-neutral alpha-alkylation of unsaturated alcohols based on a synergistic relay process involving olefin isomerization (chain walking) and umpolung hydrazone addition, which takes advantage of the interaction between the two rather inefficient individual reaction steps to enable an efficient overall process. This transformation shows the compatibility of hydrazone-type carbanions and active protons in a one-pot reaction, and at the same time achieves the first Grignard-type nucleophilic addition using olefinic alcohols as latent carbonyl groups, providing a higher yield of the corresponding secondary alcohol than the classical hydrazone addition to aldehydes does. A broad scope of unsaturated alcohols and hydrazones, including some complex structures, can be successfully employed in this reaction, which shows the versatility of this approach and its suitability as an alternative, efficient means for the generation of secondary and tertiary alcohols.
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