The Direct Rh(III)-Catalyzed C–H Amidation of Aniline Derivatives Using a Pyrimidine Directing Group: The Selective Solvent Controlled Synthesis of 1,2-Diaminobenzenes and Benzimidazoles
Shrikant M. Khake, Naoto Chatani
Abstract
The regioselective Rh(III)-catalyzed C-H amidation of aniline derivatives with dioxazolones as an amidating reagent with a pyrimidine as a directing group leading to the production of 1,2-diaminobenzene derivatives or benzimidazole derivatives is described. The product distribution is controlled by the nature of solvent used. The reaction provides a broad substrate scope for aniline derivatives with various important functional groups including dioxazolones.
Topics & Concepts
ChemistryAnilinePyrimidineBenzimidazoleRegioselectivityReagentCatalysisSubstrate (aquarium)SolventFunctional groupCombinatorial chemistryAniline CompoundsOrganic chemistryMedicinal chemistryStereochemistryGeologyOceanographyPolymerCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques