Developments in the Alkynyltrifluoromethylations of Alkenes and Alkynes

Attila M. Remete; Melinda Nonn; Balázs Volk; Loránd Kiss

doi:10.1055/a-1811-8679

Synthesis, Inhaltsverzeichnis

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

Authors

Attila M. Remete

^aInstitute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary
Melinda Nonn

^aInstitute of Pharmaceutical Chemistry, University of Szeged, 6720 Szeged, Eötvös u. 6, Hungary

^bMTA 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

^cDirectorate of Drug Substance Development, Egis Pharmaceuticals PLC, P.O. Box 100, 1475 Budapest, Hungary
Loránd Kiss ∗

^dInstitute of Organic Chemistry, Research Centre for Natural Sciences, 1117 Budapest, Magyar Tudósok krt. 2, Hungary

Abstract

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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

Volltext

Referenzen

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