Transition-Metal-Free C-N Cross-Coupling Enabled by a Multifunctional Reagent.

We report the design and development of a transition-metal-free cross-coupling reaction of phenols and primary amines using a simple and readily available multifunctional reagent. The reactions work by induced proximity and electronic activation of both the nucleophile and the electrophile for net dehydrative C-N coupling reactions. Notably, the reactions do not involve the use of a transition metal for C-N bond formation, preactivation of the phenol electrophile, or exclusion of air or moisture. The mild conditions tolerate a broad range of functional groups and allow for this to be applied to the late-stage functionalization of complex substrates with a wide scope of coupling partners.