Royal College of Surgeons in Ireland
Vinylogous Nitro-Haloform Reaction Enables Aromatic Amination.pdf (1.93 MB)

Vinylogous nitro-haloform reaction enables aromatic amination

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journal contribution
posted on 2023-09-07, 15:38 authored by Claudio Monasterolo, Mauro AdamoMauro Adamo

The first example of an aromatic haloform reaction is reported, defining a conceptually new haloform-type approach to the metal-free functionalization of arenes. We demonstrated that heteroarenes bearing a vinylogous nitromethane system, via the stage of a trichloromethane derivative, could undergo aromatic amination to produce N-functionalized arenes in quantitative yields and without the need for transition-metal catalysis. The haloform-type amination was implemented in the development of effective orthogonal N-protection strategies, establishing a new promising N-protecting reagent. 



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Published Citation

Monasterolo C, Adamo MFA. Vinylogous nitro-haloform reaction enables aromatic amination. Org Lett. 2022;24(26):4729-4733.

Publication Date

28 June 2022

PubMed ID



  • Chemistry


ACS Publications


  • Published Version (Version of Record)