A New Route to Sulfonamides via Intermolecular Radical Addition to Pentafluorophenyl Vinylsulfonate and Subsequent Aminolysis

Abstract

[reaction: see text] Various radical species generated from either the corresponding iodo- or bromo- compounds and tri-n-butyltin hydride were added in an intermolecular fashion to the activated acceptor pentafluorophenyl vinylsulfonate. The products of each reaction were then subjected to aminolysis with a variety of different amines.

Synthesis and Cross-Coupling of Sulfonamidomethyltrifluoroborates

“…These compounds are commonly synthesized by reacting sulfonyl chlorides and arylmethanamines 3. This method, which has proven to be efficient, is nevertheless hampered by the handling and storage of requisite sulfonyl chlorides each and every time a new sulfonamidomethyl target is required 4. More recently, reactions starting from sulfonic acids or sulfonate esters have been reported 5.…”

Metal-free, hydroacylation of CC and NN bonds via aerobic C–H activation of aldehydes, and reaction of the products thereof

“…The carbonyl group is a versatile moiety that can be used in various synthetic transformations and, through the work pioneered by our group, 30 PFP-sulfonates have been shown to be useful alternatives to sulfonyl chlorides for the synthesis of sulfonamides. [32][33][34][35] …”

Direct Synthesis of Sulphonates of Alcohol, Oxyma‐O‐sulphonates and Oxime‐O‐sulphonates under Microwave Irradiation

“…However, the synthesis of sulphonate esters are reported from corresponding sulphonic acids also, but by reacting with diazoalkanes, which are highly toxic, explosive and often unavailable . All of these methods involve various drawbacks such as use of toxic, expensive and less available reagents, vigorous reaction conditions, long reaction time, generation of HCl, and low yield ,. Thus, owing to the pharmaceutical and biological importance of sulphonate esters and similar compounds, it is important to develop an industrially useful and environment friendly method.…”