Issue 20, 2019

Synthesis of tri-substituted allyl alcohols via a copper/iron co-catalyzed cascade perfluoroalkylation/rearrangement of aryl propynyl ethers

Abstract

A copper/iron co-catalyzed fluoroalkylative cascade cyclization/1,4-aryl migration of aryl propynyl ethers with readily available iodoperfluoroalkane reagents for the synthesis of the corresponding perfluoroalkylated tri-substituted allyl alcohol derivatives is reported. This novel protocol provides a very mild method for the construction of perfluoroalkylated cinnamyl alcohols in one step with high regio- and stereo-selectivities. Further efficient application of this protocol is illustrated with the synthesis of 2-perfluoroalkyl-3-aryl-1H-indenes via a simple acidic workup.

Graphical abstract: Synthesis of tri-substituted allyl alcohols via a copper/iron co-catalyzed cascade perfluoroalkylation/rearrangement of aryl propynyl ethers

Supplementary files

Article information

Article type
Research Article
Submitted
03 Jul 2019
Accepted
05 Sep 2019
First published
05 Sep 2019

Org. Chem. Front., 2019,6, 3575-3579

Synthesis of tri-substituted allyl alcohols via a copper/iron co-catalyzed cascade perfluoroalkylation/rearrangement of aryl propynyl ethers

W. He, J. Yu, D. Wang, G. Ran and X. Xia, Org. Chem. Front., 2019, 6, 3575 DOI: 10.1039/C9QO00848A

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