Palladium-catalyzed direct heteroarylation of chloropyridines and chloroquinolines

The direct coupling of aryl chlorides with heteroarenes would be a considerable advantage for sustainable development due to their lower cost, lower mass, the wider diversity of available compounds and also because of the formation of only HCl associated to a base as by-product and the reduction of the number of steps to prepare these compounds. We observed that through the use of PdCl(dppb)(C3H5) as a catalyst, a range of heteroaryl derivatives undergoes coupling via C–H bond activation/functionalization reaction with chloropyridines or chloroquinolines in low to high yields. This air-stable catalyst can be used with a wide variety of substrates. The position of the chloro substituent on pyridines has a minor influence on the yields. On the other hand, the nature on the heteroaryl derivative has a large influence. The highest yields were obtained using benzoxazole, thiophene or thiazole derivatives. The coupling of chloropyridines with furans also gave the expected products, but in low to moderate yields.

Through the use of air-stable PdCl(dppb)(C3H5) as catalyst, a range of chloropyridines or chloroquinolines undergoes coupling via C–H bond activation/functionalization reaction with benzoxazole, thiazoles, furans or thiophenes in low to good yields.Figure optionsDownload as PowerPoint slide