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Catalysts 2016, 6(7), 94; doi:10.3390/catal6070094

Brønsted Acid-Catalyzed Direct Substitution of 2-Ethoxytetrahydrofuran with Trifluoroborate Salts

Faculty of Science, University of Ontario Institute of Technology, 2000 Simcoe Street North, Oshawa, ON L1H 7K4, Canada
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Academic Editor: Aurelio G. Csákÿ
Received: 29 April 2016 / Revised: 9 June 2016 / Accepted: 10 June 2016 / Published: 25 June 2016
(This article belongs to the Special Issue Metal-free Organocatalysis)
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Abstract

Metal-free transformations of organotrifluoroborates are advantageous since they avoid the use of frequently expensive and sensitive transition metals. Lewis acid-catalyzed reactions involving potassium trifluoroborate salts have emerged as an alternative to metal-catalyzed protocols. However, the drawbacks to these methods are that they rely on the generation of unstable boron dihalide species, thereby resulting in low functional group tolerance. Recently, we discovered that in the presence of a Brønsted acid, trifluoroborate salts react rapidly with in situ generated oxocarbenium ions. Here, we report Brønsted acid-catalyzed direct substitution of 2-ethoxytetrahydrofuran using potassium trifluoroborate salts. The reaction occurs when tetrafluoroboric acid is used as a catalyst to afford functionalized furans in moderate to excellent yields. A variety of alkenyl- and alkynyltrifluoroborate salts readily participate in this transformation. View Full-Text
Keywords: Brønsted acid; alkynylation; alkenylation; organotrifluoroborates; metal-free; catalysis; tetrahydrofuran (THF); ether; oxocarbenium Brønsted acid; alkynylation; alkenylation; organotrifluoroborates; metal-free; catalysis; tetrahydrofuran (THF); ether; oxocarbenium
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Fisher, K.M.; Bolshan, Y. Brønsted Acid-Catalyzed Direct Substitution of 2-Ethoxytetrahydrofuran with Trifluoroborate Salts. Catalysts 2016, 6, 94.

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