[reaction: see text] It is demonstrated that o-quinones, generated by the electrochemically driven oxidation of the catechols (1a-d) at physiological pH, are rapidly scavenged by 2-mercaptobenzoxazole (3) to give related catecholthioethers (4a-d) via an EC electrochemical mechanism pathway. The electrochemical syntheses of 4a-d have been successfully performed in one-pot in ambient conditions and in an undivided cell using an environmentally friendly method with high atom economy.
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http://dx.doi.org/10.1021/jo0508301 | DOI Listing |
Angew Chem Int Ed Engl
January 2025
Department of Chemistry, University of Missouri, 601 S College Ave, Columbia, MO 65211, USA.
Toxic organic solvents and electrolytes, traditionally indispensable for electro-organic synthesis, are now being reconsidered. In developing more sustainable electro-organic synthesis, we've harnessed the aqueous micelles as solvents and electrolyte-like structures when deformed under an electric field. The technology is showcased in synthetically highly valued hydrodefluorination reactions of difluorinated indoles.
View Article and Find Full Text PDFACS Org Inorg Au
December 2024
Medicinal Chemistry, Research and Early Development, Cardiovascular, Renal and Metabolism (CVRM), BioPharmaceuticals R&D, AstraZeneca, SE-431 83 Mölndal, Sweden.
Electro-organic chemistry presents a promising frontier in drug discovery and early development, facilitating novel reactivity aligned with green chemistry principles. Despite this, electrochemistry is not widely used as a synthesis and manufacturing tool in drug discovery or development. This overview seeks to identify key areas that require additional research to make synthetic electrochemistry more accessible to chemists in drug discovery and early development and provide potential solutions.
View Article and Find Full Text PDFACS Org Inorg Au
December 2024
Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, United States.
Organic electrosynthesis has gained much attention over the last few decades as a promising alternative to traditional synthesis methods. Electrochemical approaches offer numerous advantages over traditional organic synthesis procedures. One of the most interesting aspects of electroorganic synthesis is the ability to tune many parameters to affect the outcome of the reaction of interest.
View Article and Find Full Text PDFChempluschem
December 2024
Centre for Mechanical Engineering Materials and Processes (CEMMPRE), ARISE, Department of Chemical Engineering, University of Coimbra, Rua Sílvio Lima, Pólo II, 3030-790, Coimbra, Portugal.
J Am Chem Soc
October 2024
Department of Chemistry and Biochemistry, Queens College-CUNY, Flushing, New York 11367, United States.
Molecular photocatalysis and photoelectrocatalysis have been widely used to conduct oxidation-reduction processes ranging from fuel generation to electroorganic synthesis. We recently showed that an electrostatic potential drop across the double layer contributes to the driving force for electron transfer (ET) between a dissolved reactant and a molecular catalyst immobilized directly on the electrode surface. In this article, we report voltage-driven molecular photoelectrocatalysis with a prevalent homogeneous water oxidation catalyst, (bpy)Cu (II), which was covalently attached to the carbon surface and exhibited photocatalytic activity.
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