Iridium-Catalyzed <i>ortho</i>-C–H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand
Jialin Zeng, Morio Naito, Takeru Torigoe, Masahiro Yamanaka, Yoichiro Kuninobu
Abstract
A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-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 SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.
Topics & Concepts
ChemistryBorylationThioanisoleIridiumLigand (biochemistry)CatalysisBipyridineMedicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryArylBiochemistryCrystal structureAlkylReceptorCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsPneumocystis jirovecii pneumonia detection and treatment