Issue 62, 2014

[3+3] annulation of allylic phosphoryl-stabilized carbanions/phosphorus ylides and vinyl azides: a practice strategy for synthesis of polyfunctionalized anilines

Abstract

Tandem Michael addition and Witting or Horner–Wadsworth–Emmons olefination initiated [3+3] annulation between vinyl azides and allylic phosphorus ylides or allylic phosphoryl-stabilized carbanions has been developed. This one-pot protocol furnishes highly functionalized anilines in good to excellent yields under mild, room-temperature conditions. A rational mechanism is also proposed.

Graphical abstract: [3+3] annulation of allylic phosphoryl-stabilized carbanions/phosphorus ylides and vinyl azides: a practice strategy for synthesis of polyfunctionalized anilines

Supplementary files

Article information

Article type
Communication
Submitted
08 May 2014
Accepted
04 Jun 2014
First published
04 Jun 2014

Chem. Commun., 2014,50, 8539-8542

Author version available

[3+3] annulation of allylic phosphoryl-stabilized carbanions/phosphorus ylides and vinyl azides: a practice strategy for synthesis of polyfunctionalized anilines

S. Liu, W. Chen, J. Luo and Y. Yu, Chem. Commun., 2014, 50, 8539 DOI: 10.1039/C4CC03462G

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