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

Patel, Srilaxmi M. and P., Ermiya Prasad and Bakthadoss, Manickam and Sharada, D S (2021) Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp3)–H and C(sp2)–H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds. Organic Letters, 23 (2). pp. 257-261. ISSN 1523-7060

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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. © 2020 American Chemical Society.

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IITH Creators:

IITH Creators	ORCiD
Sharada, D S	UNSPECIFIED

Item Type:

Article

Additional Information:

We are grateful to the Council of Scientific and Industrial Research (CSIR 02(0297)/17/EMR-II), New Delhi, IIT Hyderabad for financial support. S.M.P. thanks UGC, and E.P.P. thanks CSIR New Delhi, India for the award of a research fellowship. For the cyclic voltametry studies, we thank Prof. Ch. Subrahmanyam and Dr. Palyam Subramanyam, IIT Hyderabad, India.

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

13 Sep 2022 09:19

Last Modified:

13 Sep 2022 09:19

URI:

http://raiithold.iith.ac.in/id/eprint/10561