Ipso-nitration of arylsilanes

Abstract

Arylsilanes stand as convenient, inexpensive and versatile reagents for org. synthesis. They enjoy the benefits of low toxicity, low cost and high chem. stability, when compared to other organometallic reagents such as organoboron, organomagnesium or organolithium compds. Furthermore, with the advent of novel, efficient C-H silylation methods, utilization of arylsilanes in synthesis warrants further exploration. Despite the extended research on nitroarenes prepn., ipso-nitration of organosilanes has thus far not been reported. Herein, we disclose a one-pot protocol for the ipsonitration of arylsilanes employing readily available reagents, under mild conditions. The scope and limitations of the present methods will be presented and efforts towards a tandem C-H silylation/nitration protocol will also be discussed.