Silylation of aromatic heterocycles by earth abundant transition-metal-free catalysts

A method comprising contacting an organic substrate comprising an aromatic moiety with a mixture comprising (a) at least one hydrosilane and (b) potassium hydroxide (KOH), under conditions sufficient to silylate the organic substrate, the method resulting in the formation of a silylated organic substrate, wherein the silylated organic substrate has a carbon-silicon bond in a position corresponding to a position on the aromatic moiety having a carbon-hydrogen bond, unless:

• (a) the aromatic moiety is an aryl moiety having an alkyl substituent, in which case the silylated organic substrate has a carbon-silicon bond on the carbon alpha to the aryl moiety;
• or
• (b) the aromatic moiety is one having an alkylthioether substituent, in which case the silylated organic substrate has a carbon-silicon bond on the carbon alpha to the thioether sulfur;
• or
• (c) the aromatic moiety is a pyridinyl moiety having alkyl substituents on one or both C2-and C6-positions, in which case the silylated organic substrate has a carbon-silicon bond on the carbon alpha to the pyridinyl ring;
• or
• (d) the aromatic moiety is a heteroaryl moiety comprising a 5-membered heteroaryl ring having no C—H substituents in its C-2 or C-5 position and at least one alkyl substituent in the C-2 or C-5 position, in which case the silylated organic substrate has a carbon-silicon bond on the carbon alpha to the 5-membered heteroaryl ring.