General Ir-Catalyzed N-H Insertions of Diazomalonates into Aliphatic and Aromatic Amines

Zhuang Zhong; Céline Besnard; Jérôme Lacour

doi:10.1021/acs.orglett.3c03929

General Ir-Catalyzed N-H Insertions of Diazomalonates into Aliphatic and Aromatic Amines

Org Lett. 2024 Feb 9;26(5):983-987. doi: 10.1021/acs.orglett.3c03929. Epub 2024 Jan 26.

Authors

Zhuang Zhong¹, Céline Besnard², Jérôme Lacour¹

Affiliations

¹ Department of Organic Chemistry, University of Geneva, Quai Ernest Ansermet 30, CH-1211 Genève 4, Switzerland.
² Laboratory of Crystallography, University of Geneva, Quai Ernest Ansermet 24, CH-1211 Genève 4, Switzerland.

Abstract

A general N-H insertion reactivity of acceptor-acceptor diazo malonate reagents is reported using [Ir(cod)Cl]₂ as catalyst. A large range of amines, primary and secondary, aliphatic and aromatic, is possible. Mild temperatures, perfect substrate/reactant stoichiometry, and good functional group compatibility render the process particularly attractive for the (late-stage) functionalization of amines.