Electrochemical N-acylation and N-α-ketoacylation of sulfoximines via the selective decarboxylation and dehydration of α-ketoacids

Sulfoximines are commonly found in pharmaceuticals, agrochemicals and other biologically active compounds. However, limited reports exist for their selective functionalization via green and efficient protocols. Herein, we describe an electrochemical N-acylation and N-alpha-ketoacylation of sulfoximines via the selective decarboxylation and dehydration of alpha-ketoacids. These two reactions use electricity as a traceless oxidant and alpha-ketoacid as a selective acyl or alpha-ketoacyl source. A broad range of acylated- and alpha-ketoacylated sulfoximines were isolated in good to excellent yields (up to 88% and 96% yields). Moreover, these protocols have also been applied to late-stage derivatizations of fenofibrate and can be safely conducted on a gram scale.

Automated summary

In this study, a selective functionalization method for sulfoximines via electrochemical reactions was reported. The reactions utilized electricity and α-ketoacid as traceless oxidant and functionalization reagent, respectively, and resulted in high yields of acylated and α-ketoacylated products. The method was also applied to late-stage derivatizations of fenofibrate and can be conducted on a gram scale.