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Updated: Oct 25, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Iridium-catalyzed directed ortho-C(sp2)-H amination utilizing tetrazolo[1,5-a]pyridines as nitrene surrogates
Hillol Khatua1,2, Subrata Das1,3, Souvik Nandi1
1Department of Chemistry, Indian Institute of Science Education and Research (IISER) Pune, Dr Homi Bhabha Road, Pashan, Pune - 411008, India. buddhadeb.c@iiserpune.ac.in.
Abstract:
Herein, we report an iridium-catalyzed directing group-assisted C(sp2)-H amination method using tetrazolo[1,5-a]pyridines as versatile nitrene precursors. The developed method enables the direct installation of the 2-pyridylamino functionality into an aryl unit in a single step. Substrate scope evaluation, including biologically important molecules, demonstrated a broad functional group tolerance for the reaction. Mechanistic studies suggest that the reaction proceeds through iridium-catalyzed C-H bond activation, followed by nitrenoid transfer to form the new C-N bond. Moreover, this study reports the discovery of a new method for 2-pyridine-substituted aryl amine synthesis that should find wide application in medicinal chemistry and drug discovery.
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