Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions |
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Authors: | Zsanett Szcsnyi Ferenc Fülp Sndor B
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Institution: | 1.Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary Excellence Center, Eötvös u. 6, H-6720 Szeged, Hungary;2.MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Interdisciplinary Excellence Center, Eötvös u. 6, H-6720 Szeged, Hungary;3.Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, A-8010 Graz, Austria |
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Abstract: | Bismuth subnitrate is reported herein as a simple and efficient catalyst for the atom-economical synthesis of methyl ketones via Markovnikov-type alkyne hydration. Besides an effective batch process under reasonably mild conditions, a chemically intensified continuous flow protocol was also developed in a packed-bed system. The applicability of the methodologies was demonstrated through hydration of a diverse set of terminal acetylenes. By simply switching the reaction medium from methanol to methanol-d4, valuable trideuteromethyl ketones were also prepared. Due to the ready availability and nontoxicity of the heterogeneous catalyst, which eliminated the need for any special additives and/or harmful reagents, the presented processes display significant advances in terms of practicality and sustainability. |
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Keywords: | alkynes bismuth subnitrate continuous flow alkyne hydrations methyl ketones |
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