A Ligand Developmental Approach to Palladium- Catalyzed Cross-Coupling of Polyfluoroanilines and Aryl Chlorides

Abstract

Polyfluoroaniline moieties have found extensive utility in biological inhibitors\(^{3}\), agricultural chemicals\(^{4}\) , and treatment of diseases\(^{5}\). Unfortunately, access to such potentially valuable structures are limited by current Buchwald Hartwig amination methods and their syntheses are generally avoided as a result. PAd\(_{3}\), a ligand recently developed by the Carrow group, was used in an attempt to address the difficulty of coupling polyfluoroanilines. In this work, PAd\(_{3}\) is shown to facilitate polyfluoroaniline coupling with aryl chlorides to high degrees of success at catalyst loadings unprecedented in literature. Reasons for PAd\(_{3}\)’s reactivity based on optimized reaction conditions is also rationalized.