Light-Promoted Ni-Catalyzed Cross-Coupling of Aryl Chlorides with Hydrazides: Application to the Synthesis of Rizatriptan
Fei Li, Weikang Xiong, Geyang Song, Yonggang Yan, Gang Li, Chao Wang, Jianliang Xiao, Dong Xue
Abstract
A general and highly efficient photochemical C-N coupling reaction of challenging (hetero)aryl chlorides with hydrazides is reported. Catalyzed by a Ni(II)-bipyridine complex, this reaction provides an efficient tool for the synthesis of arylhydrazines in the presence of a soluble organic amine base without an external photosensitizer. The reaction features a wide substrate range (54 examples) and excellent functional group tolerance. The method has also been successfully applied to the three-step concise synthesis of rizatriptan, an effective drug for migraine and cluster headaches.
Topics & Concepts
ChemistryArylCatalysisCombinatorial chemistrySubstrate (aquarium)Functional groupRizatriptanAmine gas treatingBase (topology)Coupling reactionOrganic chemistryAlkylPolymerOceanographyAgonistReceptorMathematicsMathematical analysisBiochemistryGeologySumatriptanRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions