Direct synthesis of sulfenamides, sulfinamides, and sulfonamides from thiols and amines

Abstract

This review provides a concise overview of the synthesis of biologically and synthetically valuable sulfenamide, sulfinamide, and sulfonamide derivatives through the direct oxidative coupling of readily available low-cost thiols and amines.

A combined experimental and computational study of ligand-controlled Chan-Lam coupling of sulfenamides

“…Conventionally, synthesis of sulfenamides predominantly relies on the construction of S–N bonds via a nucleophilic attack from amines to disulfides, sulfenyl halides or their surrogates (Fig. 1A, a , left) 17 . Moreover, dehydrogenation of amines and thiols under oxidation conditions could lead to the formation of S–N bonds, though condensation of thiols to disulfides often competes (Fig.…”

Polymerization of Primary Amines with Sulfur Monochloride to Yield Red Polymers with a Conjugated SN Backbone

“…Polythiazyl (SN) x was first synthesized in 1906 and contains alternating sulfur and nitrogen atoms along its backbone (Figure ). − It has many interesting properties such as being one of only two examples of a synthetic polymer that is metallic at room temperature under atmospheric pressure and in the absence of doping. − This polymer is also superconducting with a critical temperature of 0.3 K. − Unfortunately, its straightforward composition does not lead to simple methods to alter its structure or properties, most research has described doping with different chemicals. − This polymer has been heavily investigated since its discovery, and different methods to synthesize it and its derivatives have been developed as well as numerous potential applications that take advantage of its electrical conductivity through the alternating sulfur–nitrogen bonds. − Unfortunately, its applications are limited due to its unstable nature that leads to degradation in water or under atmospheric conditions to give a gray powder. ,,,,, Although a large diversity of small organic compounds containing sulfur–nitrogen bonds have been studied for their biological activities ,− and synthesis of transition-metal complexes, − surprisingly few polymers possess nitrogen–sulfur bonds along the backbone. ,, We recently reported the synthesis of polysulfenamides, polydiaminosulfides, and polydiaminodisulfides, but these polymers possess sp 3 hybridized carbon atoms along their backbones that interrupt conjugation. ,,,…”

Heteroaryl sulfonamide synthesis: scope and limitations

“…7,8 This widely used method suffers from the toxicity and instability of sulfonyl chloride reagents that must, in addition, be prepared using strong oxidizing and chlorinating agents. [9][10][11][12][13][14][15] To overcome such a drawback, one-pot approaches 16,17 and, more recently, the copper-catalysed arylboronic acid and DABSO-based approach 18 were developed (Fig. 1B).…”