Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 24, Pages 13649-13655Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02375
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The iridium-catalyzed C(sp(3))-H silylation of 2-alkylpyridines with hydrosilanes at the benzylic position to afford 2-(1-silylalkyl)pyridines is described. The low product yield was markedly improved by adding 3,5-dimethylpyridine. Norbornene is also an essential additive for the reaction to proceed as a hydrogen scavenger. Carbon monoxide plays an important role in the catalytic cycle as a ligand. Other transition-metal carbonyls such as Rh-4(CO)(12) and Ru-3(CO)(12) can also be used as catalysts for this C-H silylation.
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