Iridium-Catalyzed -C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand.

A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via -selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH group and the oxygen atom of the boryl ligand, control the -selectivity.