One-Pot Tandem Access to Phenothiazine Derivatives from Acetanilide and 2-Bromothiophenol <i>via</i> Rhodium-Catalyzed C–H Thiolation and Copper-Catalyzed C–N Amination
Xiyan Rui, Chao Wang, Dongjuan Si, Xuechao Hui, Keting Li, Hongmei Wen, Wei Li, Jian Liu
Abstract
A one-pot and step economic reaction involving Rh(III)-catalyzed C-H thiolation and relay Cu(II)-catalyzed C-N amination of acetanilide and 2-bromothiophenol is reported here, with several valuable phenothiazine products obtained. This synthesis protocol proceeds from easily starting materials, demonstrating high atom economy, broad substrate scope, and good yield. Furthermore, the directing group can be easily eliminated, and chlorpromazine is provided in a large scale; thus this synthesis protocol could be utilized to construct phenothiazine scaffolds.
Topics & Concepts
ChemistryAcetanilidePhenothiazineAminationCatalysisCombinatorial chemistryRhodiumYield (engineering)Substrate (aquarium)NitreneCopperTandemMedicinal chemistryOrganic chemistryMetallurgyComposite materialPharmacologyMedicineGeologyOceanographyMaterials scienceCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions