Silylations of aromatic substrates with base-activated organosilanes

A method of preparing silylated compound comprising a moiety of Formula (I) or Formula (II):

• the method comprising:
• contacting a substrate containing a
• moiety with (a) a hydrosilane of formula (R1)3-mSi(H)m+1 and (b) at least one strong base comprising an alkali metal alkoxide, an alkali metal hydride, an alkaline earth metal hydride, or potassium bis(trimethylsilyl)amide, under conditions to form the silylated compound, the method resulting in the formation of the silylated compound comprising the moiety of Formula (I) or Formula (II);
• wherein
• m is 0, 1, or 2;
• R1 is independently optionally substituted C1-12 alkyl, C1-12 heteroalkyl, or an optionally substituted 5- or 6-membered aryl or heteroaryl, and, if substituted, the substituents are independently alkyl, alkenyl, aryl, heteroaryl, hydroxyl, C1-C20 alkoxy, C5-C20 aryloxy, C2-C20 alkoxycarbonyl, C5-C20 aryloxycarbonyl, amino, optionally protected carboxyl, carboxylato, cyano, halo, phosphonato, phosphoryl, phosphanyl, phosphino, sulfonato, C1-C20 alkylsulfanyl, C5-C20 arylsulfanyl, C1-C20 alkylsulfonyl, C5-C20 arylsulfonyl, C1-C20 alkylsulfinyl, C5-C20 arylsulfinyl, sulfonamido, amido, imino, nitro, nitroso, mercapto, optionally protected formyl, C1-C20 thioester, cyanato, thiocyanato, isocyanate, thioisocyanate, carbamoyl, epoxy, styrenyl, silyl, silyloxy, silanyl, siloxazanyl, boronato, or boryl;
• X is NR2, O, or S;
• R2 is an amine protecting group, an optionally substituted alkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkaryl or optionally substituted alk-heteroaryl;
• is a heteroaromatic moiety containing y additional nitrogens in the ring structure, where y=0 or 1 when X is O or S, or y=0, 1, or 2 when X is NR2;
• and
• is an aromatic moiety containing x nitrogen atoms in the ring structure, wherein x is 0, 1, or 2.