3237-31-8Relevant articles and documents
Phosphine/Photoredox Catalyzed Anti-Markovnikov Hydroamination of Olefins with Primary Sulfonamides via α-Scission from Phosphoranyl Radicals
Chinn, Alex J.,Sedillo, Kassandra,Doyle, Abigail G.
supporting information, p. 18331 - 18338 (2021/11/10)
New strategies to access radicals from common feedstock chemicals hold the potential to broadly impact synthetic chemistry. We report a dual phosphine and photoredox catalytic system that enables direct formation of sulfonamidyl radicals from primary sulf
A Versatile Electrochemical Batch Reactor for Synthetic Organic and Inorganic Transformations and Analytical Electrochemistry
Bourne, Richard A.,Kapur, Nikil,Nicholls, Thomas P.,Schotten, Christiane,Stephen, Hamish R.,Willans, Charlotte E.,Woodward, Madeleine
, p. 1084 - 1089 (2020/07/06)
A standardized and versatile electrochemical batch reactor that has wide applicability in both organic and inorganic synthesis and analytical electrochemistry has been developed. A variety of synthetic electrochemical transformations have been performed to showcase the versatility and demonstrate the reactor, including the synthesis of five Cu(I)-NHC complexes, two Au(I)-NHC complexes, and one Fe(II)-NHC complex as well as an Fe(III)-salen complex. The reactor is based on a commercially available vial with an adapted lid, making it inexpensive and highly flexible. It features a fixed interelectrode distance, which is crucial for reproducibility, along with the ability to accommodate a variety of interchangeable electrode materials. The reactor has also been used in conjunction with a parallel plate, allowing rapid screening and optimization of an organic electrochemical transformation. Cyclic voltammetry has been performed within the reactor on a range of imidazolium salt analytes with the use of an external potentiostat. The ability to use this reactor for both analytical and synthetic organic and inorganic chemistry is enabled by a flexible and characterizable design.
Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols
Laudadio, Gabriele,Barmpoutsis, Efstathios,Schotten, Christiane,Struik, Lisa,Govaerts, Sebastian,Browne, Duncan L.,No?l, Timothy
supporting information, (2019/04/16)
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.