IBS Publications Repository: A Facile Access to Primary Alkylamines and Anilines via Ir(III)-Catalyzed C-H Amidation Using Azidoformates

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A Facile Access to Primary Alkylamines and Anilines via Ir(III)-Catalyzed C-H Amidation Using Azidoformates

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Title: A Facile Access to Primary Alkylamines and Anilines via Ir(III)-Catalyzed C-H Amidation Using Azidoformates

Subject: azidoformates, ; C-H amidation, ; iridium catalysis, ; primary alkylamines, ; primary anilines

Abstract: Described herein is the development of Ir(III)-catalyzed direct C-H amidation using azidoformates as a readily deprotectable amino source. Substrates with unactivated methyl C(sp3)-H and aromatic or olefinic C(sp2)-H bonds were smoothly reacted by the iridium-based catalyst system to provide the corresponding primary alkylamines and anilines upon the subsequent removal of N-protecting groups, such as Boc, Fmoc, Cbz, pNZ, or Troc. A brief mechanistic study and synthetic applications are also presented. © 2016 American Chemical Society