RESUMEN
Whereas aryl(trialkyl)silanes are considered to be ideal organometallic reagents for cross-coupling reactions owing to their stability, low toxicity, solubility, and easy accessibility, they are generally inert under typical cross-coupling conditions. Disclosed herein is a palladium/copper catalytic system that enables the cross-coupling of trimethyl, triethyl, tert-butyldimethyl, and triisopropyl aryl silanes with aryl bromides. This process is applicable to the sequential C-H and C-Si bond arylation of thiophenes and the synthesis of poly(thiophene-fluorene)s.
RESUMEN
Aryl(triethyl)silanes are found to undergo cross-coupling with iodoarenes in the presence of catalytic amounts of CuBr2 and Ph-Davephos, as well as cesium fluoride as a stoichiometric base. Because the silicon reagents are readily accessible through catalytic C-H silylation of aromatic substrates, the net transformation allows coupling of aromatic hydrocarbons with iodoarenes via triethylsilylation.
