Palladium-catalyzed cross-coupling reactions of 2-indolyldimethylsilanois with substituted aryl halides

A mild and general cross-coupling reaction of 2-indolylsilanols has been developed. The experimental variables that lead to successful coupling are (1) the use of sodium tert-butoxide as the activator, (2) the use of copper(l) iodide in stoichiometric quantities, and (3) the use of Pd-2(dba)(3).CHCl3 as the catalyst. Under these conditions N-(Boc)-2-indolyldimethylsilanol reacts with a variety of aromatic iodides to afford the coupling products in good yield (70-84%).