N-Formylsaccharin: A Sweet(able) Formylating Agent in Mechanochemistry

Abstract

The acylation of amines has always attracted a deep interest as a synthetic route due to its high versatility in organic chemistry and biochemical processes. The purpose of this article is to present a mechanochemical acylation procedure based on the use of acyl-saccharin derivatives, namely N-formylsaccharin, N-acetylsaccharin, and N-propionylsaccharin. This protocol furnishes a valuable solvent-free alternative to the existing processes and aims to be highly beneficial in multi-step procedures due to its rapid and user-friendly workup.

Mechanosynthesis of sulfonamides via a telescopic, environmentally friendly, and cost-effective process

“…In our uninterrupted search and interest in preparing APIs and their key intermediates by mechanochemistry, we have previously reported the mechanosynthesis of several APIs. 42–54 In this study, we discovered a promising combination between 4-nitro sulfonyl chloride 2d and amines 9 and 10 (Scheme 4), which gave access to highly suitable moieties for APIs. 55–57…”

“…In our uninterrupted search and interest in preparing APIs and their key intermediates by mechanochemistry, we have previously reported the mechanosynthesis of several APIs. [42][43][44][45][46][47][48][49][50][51][52][53][54] In this study, we discovered a promising combination between 4-nitro sulfonyl chloride 2d and amines 9 and 10 (Scheme 4), which gave access to highly suitable moieties for APIs. [55][56][57] Unfortunately, the synthetic route defined above was found to be unfairly suitable for the mechanosynthesis of pharmaceuticals (9d and 10d).…”

Ammonia Synthesis by Mechanochemistry

“…Mechanochemistry is favored as a clean and green technique, allowing reactions to be performed either entirely solvent-free or requiring a significantly reduced amount of solvent through so-called liquid-assisted grinding (LAG). [3] Its effectiveness has been demonstrated in several branches of chemistry, covering physical, [4][5][6] inorganic, [7][8][9] organic, [10][11][12][13] and pharmaceutical [14,15] chemistry. Furthermore, a recent trend urges researchers to include examples of scale-up experiments in their manuscripts to demonstrate this technology's potential applicability.…”