Synthesis 2017; 49(10): 2101-2116
DOI: 10.1055/s-0036-1589484
review
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Propargylic Fluorides toward Carbo- and Heterocycles with Mono- and gem-Difluorinated Side Chains

Ali Hachem
a   Lebanese University, Laboratory for Medicinal Chemistry and Natural Products, Faculty of Sciences (1) and PRASE-EDST, Hadath­, Beirut, Lebanon
,
Danielle Grée
b   University of Rennes 1, Institute for Chemical Sciences in Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes-Cedex, France   eMail: rene.gree@univ-rennes1.fr
,
Srivari Chandrasekhar
c   CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, Telangana, India
,
René Grée*
b   University of Rennes 1, Institute for Chemical Sciences in Rennes, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes-Cedex, France   eMail: rene.gree@univ-rennes1.fr
› Institutsangaben
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Publikationsverlauf

Received: 19. Dezember 2016

Accepted after revision: 18. Januar 2017

Publikationsdatum:
24. März 2017 (online)


Abstract

This review reports the synthesis of propargylic derivatives with alkyl chains bearing either one fluorine or a gem-difluoro system. The preparation of the different categories of fluorinated derivatives is analyzed in a systematic manner, based on the nature of substituents close to the fluorine atom(s). In the second part of this review are summarized the synthetic applications of these fluorinated propargylic intermediates, focusing mainly on the preparation of carbo- and heterocyclic derivatives.

1 Introduction

2 Synthesis of Propargylic Fluorides

3 Use of Propargylic Fluorides in the Preparation of Carbo- and Heterocycles with Fluorine-Containing Side Chains

4 Conclusions and Perspectives