Chloro/bromotrimethylsilane-Cu(NO3)2·3H2O: Safe and efficient reagent system for the decarboxylative ipso-nitration and dibromination of cinnamic acids

Abstract Further synthetic potential of halotrimethylsilane-nitrate salt mixture is revealed. A mixture of TMSX-Cu(NO 3 ) 2 ·3H 2 O system is found to be an efficient reagent system for both the decarboxylative nitration ( ipso -nitration) when X = Cl, and dibromination of cinnamic acids, with X = Br, under mild conditions. The reactions are safe and simple, affording the corresponding products ( E )- β -nitrostyrenes, and anti -2,3-dibromo-3-phenylpropanoic acids in high yields with high selectivity in a relatively short time. Use of hazardous and toxic nitrating systems such as acetyl nitrate and brominating agents such as molecular bromine can be avoided.