Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp3)-H and C(sp2)-H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds

Srilaxmi M Patel; Ermiya Prasad P; Manickam Bakthadoss; Duddu S Sharada

doi:10.1021/acs.orglett.0c03269

Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp³)-H and C(sp²)-H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds

Org Lett. 2021 Jan 15;23(2):257-261. doi: 10.1021/acs.orglett.0c03269. Epub 2020 Dec 29.

Authors

Srilaxmi M Patel¹, Ermiya Prasad P¹, Manickam Bakthadoss², Duddu S Sharada¹

Affiliations

¹ Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India.
² Department of Chemistry, Pondicherry University, Puducherry 605 014, India.

PMID: 33373256
DOI: 10.1021/acs.orglett.0c03269

Abstract

Here we have demonstrated a visible-light-mediated metal-free organic-dye-catalyzed dehydrogenative N-insertion leading to highly substituted imidazoles and privileged dihydroisoquinoline-based imidazole derivatives via C(sp³)-H and C(sp²)-H bond functionalization. A sustainable, convenient, metal-free azidation/C-H aminative cyclization approach in the absence of stoichiometric oxidants is presented. This protocol involves a rare photoinduced iminyl radical as a key intermediate for the "N" insertion.