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

Author(s) Zeng, J.; Naito, M.; Torigoe, T.; Yamanaka, M.; Kuninobu, Y.
Journal Org Lett
Date Published 2020 May 01

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.

DOI 10.1021/acs.orglett.0c00946
ISSN 1523-7052
Citation Org Lett. 2020;22(9):34853489.