Continuous flow as a benign strategy for the synthesis of Thioesters via selective C-N bond cleavage

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

“…We have recognized the potential of utilizing activated amides for the selective cleavage of C-N bonds, enabling the synthesis of primary amides, as well as a diverse array of nitrogen-containing molecules, through novel methods (Scheme 1a). [33][34][35][36][37] Based on these reports, there is a pressing need to advance the efficient conversion of amide into amides, fostering crucial functional groups with extensive applicability. This necessitates the utilization of adept reagents and methodologies to drive effective transformations.…”

The copper-catalyzed oxidative radical process of site selective C–N bond cleavage in twisted amides: batch and continuous-flow chemistry

“…50,51 Among several attractive advantages offered by continuous-flow methods for the development of a sustainable chemical process, they feature rapid reaction, enhancement of mass-and heat-transfer, minimization of reaction volumes, operational safety, improvement in the degrees of sample-and reagent-mixing and easy scalability, thus offering a potent platform for chemical innovation. 52,53 Although, the use of ground-state destabilized amide (N-acyl imides) transformations in mechanochemistry 54 and electrochemistry 55 was reported by Szostak and Amgoune. So far, the development of the transition metal-catalyzed reaction of ground-state destabilized amides (N-acyl imides) in continuous-flow chemistry has not yet been documented.…”

Ring Opening/Site Selective Cleavage in N-Acyl Glutarimide to Synthesize Primary Amides

“…To reveal the more extensive applications of the process, the base hydrolysis of twisted amides to the primary amide was examined in a continuous flow system 54,59,60 by the reaction of 1a in H 2 O/THF with LiOH•H 2 O in H 2 O. The flow setup was made using a T-shaped micromixer (M 1 , 500 μm) and a tubing reactor (R 1 , 800 μm, 200 cm).…”

“…In addition to them, N -acyl-glutarimide with a twist value (τ = 89.1°) has resonance-destabilized energy, which served as the most beneficial application that has significantly strengthened the utility of amide bond interconversion. Despite the fact that twisted amides are an essential tool for interconversion, all of the benefits inherent to the transition metal-free reaction could spur new development. − The mechanistic study reveals the site selective transamidation reactions via oxidative metal addition to the activated C–N bond in twisted amide followed by a nucleophile through the tetrahedral intermediate. − To best of our knowledge, only two reports are available for primary amides using a twisted amide.…”