Transition-metal-free silylation of aromatic compounds

A method comprising contacting an organic substrate comprising an aromatic moiety with a mixture of (a) at least one organosilane and (b) at least one strong base, under conditions sufficient to silylate the aromatic substrate;

• wherein said mixture and substrate are substantially free of transition-metal compounds;
• wherein said mixture and substrate are substantially free of water, oxygen, or both water and oxygen;
• wherein the at least one organosilane comprises an organosilane of Formula (I) or Formula (II):
• (R)4-mSi(H)m (I)
• R—[—SiH(R)—O—]n—R (II)
• where m is 1, 2, or 3;
• n is 10 to 100;
• and
• each R is independently optionally substituted C1-12 alkyl or heteroalkyl, optionally substituted C5-20 aryl or heteroaryl, optionally substituted C6-30 alkaryl or heteroalkaryl, optionally substituted C6-30 aralkyl or heteroaralkyl, optionally substituted —O—C1-12 alkyl or heteroalkyl, optionally substituted —O—C5-20 aryl or heteroaryl, optionally substituted —O—C6-30 alkaryl or heteroalkaryl, or optionally substituted —O—C6-30 aralkyl or heteroaralkyl, and, if substituted, the substituents may be phosphonato, phosphoryl, phosphanyl, phosphino, sulfonato, C1-C20 alkylsulfanyl, C5-C20 arylsulfanyl, C1-C20 alkylsulfonyl, C5-C20 arylsulfonyl, C1-C20 alkylsulfinyl, C5-C20 arylsulfinyl, sulfonamido, amino, amido, imino, nitro, nitroso, hydroxyl, C1-C20 alkoxy, C5-C20 aryloxy, C2-C20 alkoxycarbonyl, C5-C20 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 a metal-containing or metalloid-containing group, where the metalloid is Sn or Ge, where the substituents may optionally provide a tether to an insoluble or sparingly soluble support media comprising alumina, silica, or carbon;
• wherein the at least one strong base comprises:
• (a) an alkali or alkaline earth metal hydride or alkoxide;
• or
• (b) an alkali or alkaline earth metal hydride;
• or
• (c) an alkali or alkaline earth metal alkoxide;
• or
• (d) A combination thereof.