One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides was written by Davies, Alyn T.;Curto, John M.;Bagley, Scott W.;Willis, Michael C.. And the article was included in Chemical Science in 2017.Electric Literature of C9H10BrNO2 This article mentions the following:
A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described synthesis of sulfonyl fluorides, allowing rapid access to these biol. important mols. Excellent functional group tolerance is demonstrated, with the transformation successfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Electric Literature of C9H10BrNO2).
4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Electric Literature of C9H10BrNO2
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics