Mita and Sato et al. presented the dehydrogenative silylation of
8-methylquinoline and 2-(o-tolyl)pyridine catalyzed by [IrCl(cod)] 2 in refluxing
toluene (Scheme 91) [231]. The silylation of 8-methylquinoline occurred at the
methyl group in an almost quantitative yield and was directed by the quinoline
scaffold. The silylation of 2-(o-tolyl)pyridine afforded an ortho-silylated product in
quantitative yield. Later, the same group reported the dehydrogenative silylation of
2-N,N
0 -dimethylaminopyridine at the methyl group [232].
Ishiyama and Miyaura et al. developed a direct dehydrogenative silylation of
simple arenes with 1-hydrosilatrane catalyzed by an Ir-2,9-dmphen
Scheme 90 Dehydrogenative homocoupling of amines
Scheme 91 Dehydrogenative silylation of C(sp
3
)–H and C(sp
2
)–H bonds in N-heteroarenes
Iridium-Catalyzed Dehydrogenative Reactions
57