18271-19-7

Upstream product

• 18271-17-5 N-tosyl-1-naphthylamine 
• 77-78-1 dimethyl sulfate 
• 2216-68-4 N-methylnaphthalen-1-amine 
• 98-59-9 p-toluenesulfonyl chloride 
• 134-32-7 1-amino-naphthalene 
• 91-20-3 naphthalene 
• 640-61-9 N-methyl-p-toluenesulfonylamide 

Downstream Products

• 17047-31-3 4-(p-Toluolsulfonyl)-N-methylamino-1-methylnaphthalin 
• 95793-73-0 N-Methyl-2-(4-methylphenylsulfonyl)-1-naphthalinamin 

Relevant academic research and scientific papers

Electrochemical C?H Amidation of Heteroarenes with N-Alkyl Sulfonamides in Aqueous Medium

The construction of C?N bonds by free radical reactions represents a powerful synthetic approach for direct C?H amidations of arenes or heteroarenes. Developing efficient and more environmentally friendly synthetic methods for C?H amidation reactions remains highly desirable. Herein, metal-free electrochemical oxidative dehydrogenative C?H amidations of heteroarenes with N-alkylsulfonamides have been accomplished. The catalyst- and chemical-oxidant-free C?H amidation features an ample scope and employs electricity as the green and sole oxidant. A variety of heteroarenes, including indoles, pyrroles, benzofuran and benzothiophene, thereby underwent this C(sp2)?H nitrogenation. Cyclic voltammetry studies and control experiments provided evidence for nitrogen-centered radicals being directly generated under metal-free electrocatalysis.

Possibilities and Limits of the Carbanionically Induced Sulfonamide-Aminosulfone Rearrangement

When transfering the title reaction to the 2- and 1-naphthyltoluenesulfonamides 5 and 10, the -shift of the arylsulfonyl group proceeds into the 3- and 2-position (to give 9 and 12, respectively), which is in full compliance with optimal conjugative and steric conditions for the relevant intermediates 8 and 11.Attemps to initiate comparable -rearrangements through the o-lithiated biphenyl derivative 17 and the p-lithiated N-phenyltoluenesulfonamide 23 led again, after extended transmetalation cascades, to the conventional -rearrangement products 22 and 32, respectively.In attempting to cause in the o-tolylbenzenesulfonamide 49 an anionically induced -sulfonyl shift into the benzyl position, two fragments of the starting molecule combined to give the novel heteropolycycle 51.Finally, it could be shown that contrary to the literature, the sulfonamides 46 and 57 rearrange also photolytically to the o-aminosulfones 45 and 58.