Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols
Author(s) -
Gabriele Laudadio,
Efstathios Barmpoutsis,
Christiane Schotten,
Lisa Struik,
Sebastian Govaerts,
Duncan L. Browne,
Timothy Noël
Publication year - 2019
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.9b02266
Subject(s) - chemistry , reagent , combinatorial chemistry , sulfonamide , electrochemistry , oxidative phosphorylation , catalysis , oxidative coupling of methane , functional group , organic chemistry , electrode , biochemistry , polymer
Sulfonamides are key motifs in pharmaceuticals and agrochemicals, spurring the continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts and can be carried out in only 5 min. Hydrogen is formed as a benign byproduct at the counter electrode. Owing to the mild reaction conditions, the reaction displays a broad substrate scope and functional group compatibility.
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