Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions

Szécsényi, Zsanett; Fülöp, Ferenc; Ötvös, Sándor B.

doi:10.3390/molecules26102864

Open AccessArticle

Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions

by

Zsanett Szécsényi

¹,

Ferenc Fülöp

^1,2,*

and

Sándor B. Ötvös

^2,3,*

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

^*

Authors to whom correspondence should be addressed.

Molecules 2021, 26(10), 2864; https://doi.org/10.3390/molecules26102864

Submission received: 24 April 2021 / Revised: 1 May 2021 / Accepted: 8 May 2021 / Published: 12 May 2021

(This article belongs to the Special Issue Advances in Flow Chemistry)

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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.

Keywords: alkynes; bismuth subnitrate; continuous flow; alkyne hydrations; methyl ketones

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MDPI and ACS Style

Szécsényi, Z.; Fülöp, F.; Ötvös, S.B. Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions. Molecules 2021, 26, 2864. https://doi.org/10.3390/molecules26102864

AMA Style

Szécsényi Z, Fülöp F, Ötvös SB. Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions. Molecules. 2021; 26(10):2864. https://doi.org/10.3390/molecules26102864

Chicago/Turabian Style

Szécsényi, Zsanett, Ferenc Fülöp, and Sándor B. Ötvös. 2021. "Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions" Molecules 26, no. 10: 2864. https://doi.org/10.3390/molecules26102864

APA Style

Szécsényi, Z., Fülöp, F., & Ötvös, S. B. (2021). Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions. Molecules, 26(10), 2864. https://doi.org/10.3390/molecules26102864

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Bismuth Subnitrate-Catalyzed Markovnikov-Type Alkyne Hydrations under Batch and Continuous Flow Conditions

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