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Synthesis 2022; 54(17): 3753-3760
DOI: 10.1055/a-1811-8679
special topic
Special Issue in memory of Prof. Ferenc Fülöp

Developments in the Alkynyltrifluoromethylations of Alkenes and Alkynes

Attila M. Remete
a   Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
,
Melinda Nonn
a   Institute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
b   MTA TTK Lendület Artificial Transporter Research Group, Institute of Materials and Environmental Chemistry, Research Center for Natural Sciences, Hungarian Academy of Sciences, Magyar Tudósok krt. 2, 1117 Budapest, Hungary
,
Balázs Volk
c   Directorate of Drug Substance Development, Egis Pharmaceuticals PLC, P.O. Box 100, 1475 Budapest, Hungary
,
Loránd Kiss  ∗
d   Institute of Organic Chemistry, Research Centre for Natural Sciences, 1117 Budapest, Magyar Tudósok krt. 2, Hungary
› Author AffiliationsWe are grateful to the Nemzeti Kutatási Fejlesztési és Innovációs Hivatal (Hungarian Research Foundation; NKFIH FK 134586) for financial support.
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Abstract

As a consequence of the expanding relevance of fluorine-containing organic molecules in drug research, the synthesis of organofluorine scaffolds has high significance in synthetic organic chemistry. Trifluoromethylative difunctionalizations of carbon–carbon multiple bonds, with the simultaneous introduction of a CF3 group and another function, have considerable potential. Considering the high importance of carbon–carbon bond-forming reactions in organic synthesis, carbotrifluoromethylations and, in particular, alkynyltrifluoromethylations have increasing interest in synthetic chemistry. Alkynyltrifluoromethylation is a narrow area and a relatively new approach in synthetic chemistry­; however it has not been reviewed so far. Our goal in this short review is to summarize recent developments in alkynyltrifluoromethylation reactions by considering: (a) alkynyltrifluoromethylation reactions of alkenes, including reactions involving either intramolecular alkynyl migration or intermolecular transformation, and (b) alkynyltrifluoromethylation reactions of alkynes.

1 Introduction

2 Alkynyltrifluoromethylation Reactions of Alkenes

2.1 Reactions Involving Intramolecular Alkynyl Migration

2.2 Intermolecular Reactions

3 Alkynyltrifluoromethylation Reactions of Alkynes

4 Summary and Outlook

Keywords

alkenes - difunctionalization - fluorine - photocatalysis - trifluoromethylation


Publication History

Received: 10 March 2022

Accepted after revision: 30 March 2022

Accepted Manuscript online:
30 March 2022

Article published online:
12 May 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
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