Base-Promoted Formal [4 + 3] Annulation between 2-Fluorophenylacetylenes and Ketones: A Route to Benzoxepines.

doi:10.1021/acs.joc.5b02487

Paper

Base-Promoted Formal [4 + 3] Annulation between 2-Fluorophenylacetylenes and Ketones: A Route to Benzoxepines.

Published Jan 21, 2016 · Lu Ouyang, Chaorong Qi, Hai-Yu He

The Journal of organic chemistry

Q2 SJR score

27

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

The first base-promoted formal [4 + 3] annulation between 2-fluorophenylacetylenes and ketones has been disclosed. The reaction proceeds through a tandem α-vinylation of ketones followed by an intramolecular nucleophilic aromatic substitution (SNAr) reaction of the in situ generated β,γ-unsaturated ketone intermediates, providing a straightforward access to a wide range of functionalized benzoxepines in moderate to high yields. The transition-metal-free methodology featured a wide substrate scope, the use of easily available starting materials, and a high functional group tolerance.

Study Snapshot

Base-promoted formal [4 + 3] annulation between 2-fluorophenylacetylenes and ketones provides a straightforward access to a wide range of functionalized benzoxepines in moderate to high yields, with easy substrate scope and high functional group tolerance.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Base-Promoted Formal [4 + 3] Annulation between 2-Fluorophenylacetylenes and Ketones: A Route to Benzoxepines.

References

Citations