Redox-neutral ortho-C-H amination of pinacol arylborates via palladium(ii)/norbornene catalysis for aniline synthesis.

ABSTRACT: A palladium(ii)/norbornene cooperative catalysis enabled redox-neutral ortho-C-H amination of pinacol aryl- or heteroarylborates for the synthesis of structurally diverse anilines is reported. This method is scalable, robust (tolerance of air and moisture), phosphine ligand-free, and compatible with a wide range of functionalities. These practical features make this reaction amenable for industry. A plethora of synthetically very useful halogenated anilines, which often cannot be prepared via other transition-metal-catalyzed aminations, are readily produced using this method. Particularly, the orthogonal reactivity between pinacol arylborates and aryl iodides is demonstrated. Preliminary deuterium-labeling studies reveal a redox-neutral ipso-protonation mechanism of this process, which wil

SUBMITTER: Chen S 

PROVIDER: S-EPMC6839810 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature