Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 34, Pages 9944-9947Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201503704
Keywords
C-H activation; cobalt; heterocycles; homogeneous catalysis; transition metals
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Funding
- ACT-C program from JST
- Toray Science Foundation
- Naito Foundation
- JSPS
- Grants-in-Aid for Scientific Research [26105756, 13J10837] Funding Source: KAKEN
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The unique reactivity of [Cp*Co-III] over [Cp*Rh-III] was demonstrated. A cationic [Cp*Co-III] catalyst promoted direct dehydrative C-H allylation with non-activated allyl alcohols, thus giving C2-allylated indoles, pyrrole, and phenylpyrazole in good yields, while analogous [Cp*Rh-III] catalysts were not effective. The high g-selectivity and C2-selectivity indicated that the reaction proceeded by directing-group-assisted C-H metalation. DFT calculations suggested that the gamma-selective substitution reaction proceeded by C-H metalation and insertion of a C-C double bond, with subsequent beta-hydroxide elimination. The [Cp*Co-III] catalyst favored beta-hydroxide elimination over beta-hydride elimination.
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