Volume 23, Issue 62 p. 15628-15632
Communication

Palladium-Catalyzed 2,2,2-Trifluoroethoxylation of Aromatic and Heteroaromatic Chlorides Utilizing Borate Salt and the Synthesis of a Trifluoro Analogue of Sildenafil

Bálint Pethő

Bálint Pethő

MTA-ELTE “Lendület” Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University, Faculty of Science, Pázmány Péter stny. 1/A, 1117 Budapest, Hungary

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Márton Zwillinger

Márton Zwillinger

MTA-ELTE “Lendület” Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University, Faculty of Science, Pázmány Péter stny. 1/A, 1117 Budapest, Hungary

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János T. Csenki

János T. Csenki

MTA-ELTE “Lendület” Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University, Faculty of Science, Pázmány Péter stny. 1/A, 1117 Budapest, Hungary

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Anna E. Káncz

Anna E. Káncz

Compound Profiling Laboratory, Gedeon Richter Plc., Gyömrői út 19–21, 1103 Budapest, Hungary

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Dr. Balázs Krámos

Dr. Balázs Krámos

Spectroscopic Research Division, Gedeon Richter Plc., Gyömrői út 19–21, 1103 Budapest, Hungary

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Judit Müller

Judit Müller

Compound Profiling Laboratory, Gedeon Richter Plc., Gyömrői út 19–21, 1103 Budapest, Hungary

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Dr. György T. Balogh

Dr. György T. Balogh

Compound Profiling Laboratory, Gedeon Richter Plc., Gyömrői út 19–21, 1103 Budapest, Hungary

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Dr. Zoltán Novák

Corresponding Author

Dr. Zoltán Novák

MTA-ELTE “Lendület” Catalysis and Organic Synthesis Research Group, Institute of Chemistry, Eötvös University, Faculty of Science, Pázmány Péter stny. 1/A, 1117 Budapest, Hungary

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First published: 08 September 2017
Citations: 17

Graphical Abstract

Fluorine Blue: A novel palladium-catalyzed trifluorethyoxylation of aryl chlorides was developed with the aid of a new type of borate-based trifluoroethoxylating reagent. Beyond the functionalization of various aromatic and heteroaromatic systems, the synthesis of the trifluoro analogue of Sidenafil (Viagra) was achieved together with the determination of its physicochemical properties.

Abstract

A simple and convenient method was developed for the introduction of a 2,2,2-trifluoroethoxy group to various aromatic and heteroaromatic systems. The novel process utilizes aromatic chlorides as substrates, and tetrakis(2,2,2-trifluoroethoxy) borate salt as an inexpensive and readily available fluoroalkoxy source in a palladium-catalyzed cross-coupling reaction. The power of the developed methodology was demonstrated in the synthesis of a fluorous derivative of Sildenafil.