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Chemical Science

Aromatization-driven deconstructive functionalization of spiro dihydroquinazolinones via dual photoredox/nickel catalysis†

Hong-Jie Miao,a   Jin-Hua Zhang,a   Wenke Li,a   Wenpeng Yang,a   Hong Xin,a   Pin Gao, ORCID logo a   Xin-Hua Duan ORCID logo a  and  Li-Na Guo ORCID logo *a  

* Corresponding authors

a School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Jiaotong University, Xi'an 710049, China
E-mail: guoln81@xjtu.edu.cn

Abstract

Aromatization-driven deconstruction and functionalization of spiro dihydroquinazolinones via dual photoredox/nickel catalysis is developed. The aromatization effect was introduced to synergistically drive unstrained cyclic C–C bond cleavage, with the aim of overcoming the ring-size limitation of nitrogen-centered radical induced deconstruction of carbocycles. Herein, we demonstrate the synergistic photoredox/nickel catalyzed deconstructive cross-coupling of spiro dihydroquinazolinones with organic halides. Remarkably, structurally diverse organic halides including aryl, alkenyl, alkynyl, and alkyl bromides were compatible for the coupling. In addition, this protocol is also characterized by its mild and redox-neutral conditions, excellent functional group compatibility, high atom economy, and easy scalability. A telescoped procedure involving condensation and ring-opening/coupling was found to be accessible. This work provides a complementary strategy to the existing radical-mediated C–C bond cleavage of unstrained carbocycles.

Graphical abstract: Aromatization-driven deconstructive functionalization of spiro dihydroquinazolinones via dual photoredox/nickel catalysis

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Article information

DOI
https://doi.org/10.1039/D4SC01111B
Article type
Edge Article
Submitted
16 Feb 2024
Accepted
07 May 2024
First published
08 May 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2024, Advance Article

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Aromatization-driven deconstructive functionalization of spiro dihydroquinazolinones via dual photoredox/nickel catalysis

H. Miao, J. Zhang, W. Li, W. Yang, H. Xin, P. Gao, X. Duan and L. Guo, Chem. Sci., 2024, Advance Article , DOI: 10.1039/D4SC01111B

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