Electrochemical Multicomponent Synthesis of Alkyl Alkenesulfonates using Styrenes, SO 2 and Alcohols.

Autor: de A Bartolomeu A; Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.; Institute of Chemistry, University of Campinas, 13083-970, Campinas, SP, Brazil., Breitschaft FA; Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany., Schollmeyer D; Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany., Pilli RA; Institute of Chemistry, University of Campinas, 13083-970, Campinas, SP, Brazil., Waldvogel SR; Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.; Institute of Biological and Chemical Systems - Functional Molecular Systems (IBCS FMS), Kaiserstraße 12, 76131, Karlsruhe, Germany.; Max-Planck-Institute for Chemical Energy Conversion, Stiftstraße 34-36, 45470, Mülheim an der Ruhr, Germany.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Apr 11; Vol. 30 (21), pp. e202400557. Date of Electronic Publication: 2024 Feb 27.
DOI: 10.1002/chem.202400557
Abstrakt: A novel electrochemical approach to access alkyl alkenesulfonates via a multicomponent reaction was developed. The metal-free method features easy-to-use SO 2 stock solution forming monoalkylsulfites from alcohols with an auxiliary base in-situ. These intermediates serve a dual role as starting materials and as supporting electrolyte enabling conductivity. Anodic oxidation of the substrate styrene, radical addition of these monoalkylsulfites and consecutive second oxidation and deprotonation preserve the double bond and form alkyl β-styrenesulfonates in a highly regio- and stereoselective fashion. The feasibility of this electrosynthetic method is demonstrated in 44 examples with yields up to 81 %, employing various styrenes and related substrates as well as a diverse set of alcohols. A gram-scale experiment underlines the applicability of this process, which uses inexpensive and readily available electrode materials.
(© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
Externí odkaz: