Divergence in Ynone Reactivity: Atypical Cyclization by 3,4‐Difunctionalization versus Rare Bis(cyclization)

Divergence in Ynone Reactivity: Atypical Cyclization by 3,4‐Difunctionalization versus Rare... Functionalized ynones can be activated by Tf2C=CH2, which was generated in situ, to form zwitterionic species. These species were trapped in an intramolecular fashion by several nucleophiles to generate two major types of triflones in a divergent manner. Through fine‐tuning of the reaction temperature, bis(triflyl)‐6‐membered‐ or (triflyl)‐5‐membered‐fused‐heterocycles were achieved in reasonable yields in a totally selective manner. In this way, bis(triflyl)flavones, bis(triflyl)thioflavones, bis(triflyl)selenoflavones, (triflyl)benzothienopyrans, (triflyl)benzoselenophenopyrans, (triflyl)vinyl aurones, and (triflyl)pyranoindoles were constructed. Conceivable mechanistic pathways were suggested on the basis of the isolation of several intermediates and the results from control experiments. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry - A European Journal Wiley

Divergence in Ynone Reactivity: Atypical Cyclization by 3,4‐Difunctionalization versus Rare Bis(cyclization)

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Publisher
Wiley Subscription Services, Inc., A Wiley Company
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
0947-6539
eISSN
1521-3765
D.O.I.
10.1002/chem.201800630
Publisher site
See Article on Publisher Site

Abstract

Functionalized ynones can be activated by Tf2C=CH2, which was generated in situ, to form zwitterionic species. These species were trapped in an intramolecular fashion by several nucleophiles to generate two major types of triflones in a divergent manner. Through fine‐tuning of the reaction temperature, bis(triflyl)‐6‐membered‐ or (triflyl)‐5‐membered‐fused‐heterocycles were achieved in reasonable yields in a totally selective manner. In this way, bis(triflyl)flavones, bis(triflyl)thioflavones, bis(triflyl)selenoflavones, (triflyl)benzothienopyrans, (triflyl)benzoselenophenopyrans, (triflyl)vinyl aurones, and (triflyl)pyranoindoles were constructed. Conceivable mechanistic pathways were suggested on the basis of the isolation of several intermediates and the results from control experiments.

Journal

Chemistry - A European JournalWiley

Published: Jan 7, 2018

Keywords: ; ; ; ;

References

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