Photo- and dioxygen-enabled radical C(sp3)–N(sp2) cross-coupling between guanidines and perfluoroalkyl iodides

Shulin Liu; Rui Wang; Bo Zhu; Wei Guan; Fushun Liang

doi:10.1039/C9OB01520E

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Photo- and dioxygen-enabled radical C(sp³)–N(sp²) cross-coupling between guanidines and perfluoroalkyl iodides†

Shulin Liu,^a Rui Wang,

*^b Bo Zhu,^c Wei Guan

^c and Fushun Liang

*^a

Author affiliations

* Corresponding authors

^a College of Chemistry, Liaoning University, Shenyang 110036, China
E-mail: fsliang@lnu.edu.cn

^b Institute of Petrochemical Technology, Jilin Institute of Chemical Technology, Jilin 132022, China
E-mail: 345734719@qq.com

^c Faculty of Chemistry, Northeast Normal University, Changchun 130024, China

Abstract

A photo- and dioxygen-enabled intermolecular radical C_sp³–N_sp² cross-coupling between guanidines and perfluoroalkyl iodides has been developed. N²-Perfluoroalkacylguanidines, which are of biological importance, were obtained under mild conditions via N_sp²-perfluoroalkylation and subsequent hydrolysis. The role of dioxygen in the reaction system was tentatively elucidated; it was supposed to act as an electron shuttle (redox mediator).

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB01520E
Article type: Communication
Submitted: 09 Jul 2019
Accepted: 05 Sep 2019
First published: 09 Sep 2019

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Org. Biomol. Chem., 2019,17, 8695-8700

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Photo- and dioxygen-enabled radical C(sp³)–N(sp²) cross-coupling between guanidines and perfluoroalkyl iodides

S. Liu, R. Wang, B. Zhu, W. Guan and F. Liang, Org. Biomol. Chem., 2019, 17, 8695 DOI: 10.1039/C9OB01520E

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Organic & Biomolecular Chemistry