Synlett
DOI: 10.1055/s-0036-1589057
letter
© Georg Thieme Verlag Stuttgart · New York

Hydrogen-Bond-Promoted Friedel–Crafts Reaction of Secondary Propargylic Fluorides: Preparation of 1-Alkyl-1-aryl-2-alkynes

Jean-Denys Hamel, Meggan Beaudoin, Mélissa Cloutier, Jean-François Paquin*
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Publication History

Received: 20 April 2017

Accepted after revision: 29 May 2017

Publication Date:
06 July 2017 (eFirst)

Dedicated to Prof. Victor Snieckus on the occasion of his 80th birthday

Abstract

We report that aromatic propargylation is achievable with secondary propargylic fluorides, thus affording 1-alkyl-1-aryl-2-alkynes. In the present case, hydrogen bonding is responsible for the activation of the C–F bond. A large excess of arene nucleophile is shown to be necessary to achieve good yields.

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