Synthesis of N-Aryl Carbamates from Aryl(TMP)iodonium Salts via C–N Coupling

Modular C–N coupling is a desirable way to construct N-aryl carbamates, which are privileged scaffolds in active pharmaceutical ingredients. However, there are no broadly applicable metal-free methods for theN-arylation of carbamates. Herein, we describe a metal-free approach that uses aryl(TMP)iodonium salts as arylation reagents for cyclic carbamates by exploiting the metal-like reactivity of iodine(III). The scope includes 25 examples, including 17 different aryl(TMP)iodonium salts and 9 different carbamates, in yields ranging between 55 and 97% (75% avg).