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

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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

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Publication details

The article was received on 03 Jul 2019, accepted on 05 Sep 2019 and first published on 05 Sep 2019


Article type: Research Article
DOI: 10.1039/C9QO00848A
Org. Chem. Front., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9QO00848A

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