A methyl group of methylchlorosilanes undergoes C-H borylation in an iridium-catalyzed reaction with bis(pinacolato)diboron in cyclohexane at 80 °C, giving (borylmethyl)chlorosilanes selectively.
In the presence of an iridium 3,4,7,8-tetramethyl-1,10-phenanthroline
catalyst, a methyl group on the silicon atom of alkyltrimethylsilanes
undergoes selective C–H borylation with bis(pinacolato)diboron
in cyclooctane at 135 °C to give alkyl(borylmethyl)dimethylsilanes.
The C–H borylation of tetramethylsilane takes place efficiently
at 100 °C. Permethyloligosilanes can also undergo C–H
borylation without cleavage of the Si–Si bonds.
The C(sp(3))-H bonds located on the methyl groups of an isopropyl group participate in iridium-catalysed C-H borylation with bis(pinacolato)diboron via a significant rate acceleration caused by a catalytic amount of t-BuOK.
Highly enantioselective cycloisomerization of N-methylanilines, bearing o-alkenyl groups, into indolines is established. An iridium catalyst bearing a bidentate chiral diphosphine effectively promotes the intramolecular addition of the C(sp )-H bond across a carbon-carbon double bond in a highly enantioselective fashion. The reaction gives indolines bearing a quaternary stereogenic carbon center at the 3-position. The reaction mechanism involves rate-determining oxidative addition of the N-methyl C-H bond, followed by intramolecular carboiridation and subsequent reductive elimination.
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