Gold(I)-catalyzed direct C–H arylation of pyrazine and pyridine with aryl bromides

Abstract

An efficient procedure for the direct C–H arylation of electron-poor aromatics such as pyrazine and pyridine with aryl bomides is described. In the presence of catalytic amount of Cy 3PAuCl and with the use of t-BuOK as base, pyrazine undergoes the direct C–H arylation with aryl bromides at 100 °C, and the yields of the arylated products depend on the nature of aryl bromides. In the cases of electron-rich aryl bromides used, the arylated pyrazines can be obtained in good to high yields. For electron-poor aryl bromides, the addition of AgBF 4 is the crucial point to accelerate the coupling reaction to give the arylated products in moderate yields. Pyridine also reacts with electron-rich aryl bromides catalyzed by Cy 3PAuCl to give a mixture of arylated regioisomers in moderate yield. However, in order to realize the direct C–H arylation of pyridine with electron-poor aryl bromides, the addition of silver salt as additive and a milder reaction temperature (60 °C) are required.