The preparation of π-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables:(1) identification of stable, isolable alkali metal silanolates,(2) identification of conditions for preformation and isolation of silanolate salts,(3) judicious choice in the ...