Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine syntheses via Csp3–H functionalizations

Navdeep Kaur; Elizabeth C. Ziegelmeyer; Olutayo N. Farinde; Jonathon T. Truong; Michelle M. Huynh; Wei Li

doi:10.1039/D1CC04588A

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Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine syntheses via C_sp³–H functionalizations†

Navdeep Kaur,^a Elizabeth C. Ziegelmeyer,^a Olutayo N. Farinde,^a Jonathon T. Truong,^a Michelle M. Huynh

^a and Wei Li

*^a

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* Corresponding authors

^a Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, Toledo, Ohio 43606, USA
E-mail: wei.li@utoledo.edu

Abstract

A catalytic benzylic C_sp³–H functionalization protocol is described here. This visible light-mediated process is centered on the utilization of a bromide catalyst and oxidant to generate a nitrogen (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of C_sp³–H bonds that enabled the stereoselective synthesis of cis- and trans-oxazolines.

This article is part of the themed collection: 2021 Emerging Investigators

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Article information

DOI: https://doi.org/10.1039/D1CC04588A
Article type: Communication
Submitted: 19 Aug 2021
Accepted: 14 Sep 2021
First published: 14 Sep 2021

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Chem. Commun., 2021,57, 10387-10390

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Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine syntheses via C_sp³–H functionalizations

N. Kaur, E. C. Ziegelmeyer, O. N. Farinde, J. T. Truong, M. M. Huynh and W. Li, Chem. Commun., 2021, 57, 10387 DOI: 10.1039/D1CC04588A

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