Photoredox β-C(sp3)–H heteroarylation of o-iodoaryl-alkan-1-ones with heteroarenes via HAT and dual C–H functionalizations

Guang-Chuan Xu; Liang Zeng; Ming Hu; Fu-Jin Sun; Jin-Heng Li

doi:10.1039/D5QO00147A

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Photoredox β-C(sp³)–H heteroarylation of o-iodoaryl-alkan-1-ones with heteroarenes via HAT and dual C–H functionalizations†

Guang-Chuan Xu,^a Liang Zeng,*^a Ming Hu,^a Fu-Jin Sun*^a and Jin-Heng Li

*^abc

Author affiliations

* Corresponding authors

^a State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
E-mail: loey_zengliang@hnu.edu.cn, sunfujin@qust.edu.cn, jhli@hnu.edu.cn

^b State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

^c School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 475004, China

Abstract

A synthetically useful method for the formal β-heteroarylation of ketones via an iodoarene-directed photoredox remote C(sp³)–H heteroarylation of o-iodoarylalkan-1-ones with heteroarenes is reported. This protocol relies on single electron transfer (SET), hydrogen atom transfer (HAT) and dual C–H functionalizations leading to β-heteroaryl ketones. This mild method displays broad scope, good functional group compatibility, high atom economy and excellent selectivity control.

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Article information

DOI: https://doi.org/10.1039/D5QO00147A
Article type: Research Article
Submitted: 21 Jan 2025
Accepted: 13 Feb 2025
First published: 15 Feb 2025

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Org. Chem. Front., 2025, Advance Article

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Photoredox β-C(sp³)–H heteroarylation of o-iodoaryl-alkan-1-ones with heteroarenes via HAT and dual C–H functionalizations

G. Xu, L. Zeng, M. Hu, F. Sun and J. Li, Org. Chem. Front., 2025, Advance Article , DOI: 10.1039/D5QO00147A

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