Silylation of aromatic heterocycles by disilanes using potassium alkoxide catalysts

A method comprising contacting an organic substrate having a heteroaromatic moiety with a mixture comprising (a) at least one organodisilane and (b) at least one potassium alkoxide base, in the presence of an organic solvent having an oxygen donor group, under conditions sufficient to silylate the organic substrate, the method resulting in a heteroaromatic silylated product, wherein the at least one organodisilane comprises an organodisilane of Formula (I):

• (R)3Si—Si(R)3 (I)
• wherein:
• each R is independently H, C1-12 alkyl, C1-12 heteroalkyl, C2-12 alkenyl, C2-12 heteroalkenyl, C2-12 alkynyl, heteroalkynyl, C6-20 aryl, C3-20 heteroaryl, C7-30 alkaryl, C6-30 heteroalkaryl, C7-30 aralkyl, C5-30 heteroaralkyl, —O—C1-12 alkyl, —O—C1-12 heteroalkyl, —O—C6-20 aryl, —O—C3-20 heteroaryl, —O—C7-30 alkaryl, —O—C5-30 heteroalkaryl, —O—C7-30 aralkyl, or —O—C5-30 heteroaralkyl, and wherein
• each C1-12 alkyl, C1-12 heteroalkyl, C2-12 alkenyl, C2-12 heteroalkenyl, C2-12 alkynyl, heteroalkynyl, C6-20 aryl, C3-20 heteroaryl, C7-30 alkaryl, C6-30 heteroalkaryl, C7-30 aralkyl, C5-30 heteroaralkyl, —O—C1-12 alkyl, —O—C1-12 heteroalkyl, —O—C6-20 aryl, —O—C3-20 heteroaryl, —O—C7-30 alkaryl, —O—C5-30 heteroalkaryl, —O—C7-30 aralkyl, or —O—C5-30 heteroaralkyl is optionally substituted with phosphonato, phosphoryl, phosphino, sulfonato, C1-C20 alkylsulfanyl, C6-20 arylsulfanyl , C1-C20 alkylsulfonyl, C6-20 arylsulfonyl, C1-C20 alkylsulfinyl, C6-20 arylsulfinyl, sulfonamido, amino, amido, imino, nitro, nitroso, hydroxyl, C1-C20 alkoxy, C6-20 aryloxy, C2-C20 alkoxycarbonyl, C6-20 aryloxycarbonyl, carboxyl, carboxylato, mercapto, formyl, C1-C20 thioester, cyano, cyanato, thiocyanato, isocyanate, thioisocyanate, carbamoyl, epoxy, styrenyl, silyl, silyloxy, silanyl, siloxazanyl, boronato, boryl, or halogen, or where the substituents optionally provide a tether to an insoluble or sparingly soluble support media comprising alumina, silica, or carbon.