Efficient Synthesis of Symmetrical and Unsymmetrical Disulfides Using a Continuous Flow Method

Abstract

This study described an efficient synthesis of disulfide from two thiols in a continuous flow reactor, using 1-chlorobenzotriazole (BtCl) as an oxidant. It has been demonstrated that this method is feasible with a variety of aliphatic and aromatic thiols to produce a corresponding disulfide under mild conditions. Productivity of this process is determined by a high yield, a wide range of functional group compatibility, and the fact that disulfide is readily available in a short timeframe. This method enables the simple synthesis of a series of symmetrical and unsymmetrical disulfides.

Striped Phase Formations of Alkanethiols in Au(111)/Graphene/SAM and Au(111)/SAM/Graphene Heterolayered Structures: Insights from vdW-DFT Calculations

“…The disulfide bonds, having a covalent character, are formed as a result of oxidation of thiol termini in cysteine units of protein structures, playing an important role in biological and chemical processes . The experimental studies investigating the formation mechanisms of symmetric/antisymmetric disulfide bonds between organic/inorganic molecular structures have reported various reaction steps. − While dependent on the molecular framework, computational studies have indicated that the molecular disulfide (R–S–S–R) bond has an approximate length of 2.0 Å and that the dissociation energies of intermolecular disulfide bonds range from 40 to 70 kcal/mol. − Our findings of this study are in good agreement with these data. For the (12 × √3)-GR30° head-to-head ordered decanethiol striped phase in Figure (c), the disulfide bond between dimerized decanethiols was found to be 2.03 Å, and the intermolecular bond dissociation energy was calculated as 1.91 eV (44.04 kcal/mol).…”

Catalyst-free activation of N–C(O) Amide bonds – efficient cascade synthesis of N-acyl thiocarbamides in batch and continuous-flow

“…Despite recent advancements, significant progress has been achieved in continuous-flow chemistry. [56][57][58][59] These methods provide several benefits for sustainable chemical processes, such as operational safety, rapid reactions, improved massand heat-transfer, minimization of reaction volumes, improvement in the degrees of sample-and reagent-mixing and easy scalability, thus offering a potent platform for chemical innovation. 60,61 Hence, our laboratory has focused on developing new methods for selectively cleaving C-N bonds in amides using both batch and continuous-flow processes.…”

Continuous-Flow Synthesis of Arylthio-Cyclopropyl Carbonyl Compounds

“…On the other hand, the continuous-flow synthesis of sulfur-containing adducts from thiols has been successfully performed, highlighting the advantages of these methods [27,28]. Nevertheless, a certain number of continuous-flow cyclopropane derivative synthesis methods have been reported by several authors in the last decade, including light-mediated borocyclopropanation [29] and ethyldiazoacetate addition to styrene [30,31] and the transition-metal-catalyzed synthesis of cyclopropyl phosphonates [32], and esters have been also achieved [33]. However, up-to-date continuous-flow processes for the synthesis of arylthio cyclopropyl derivatives from HCB C4-C3 ring contraction are unreported.…”