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Updated: May 31, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Synthesis of N-Aryl Carbamates from Aryl(TMP)iodonium Salts via C-N Coupling
Joseph Hatton1, David R Stuart1
1Department of Chemistry, Portland State University, Portland, Oregon 97201, United States.
Abstract:
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).
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