Direct C–H functionalization of difluoroboron dipyrromethenes (BODIPYs) at β-position by iodonium salts

Wenming Ren; Huaijiang Xiang; Chengyuan Peng; Zulipali Musha; Jingjing Chen; Xin Li; Ruimin Huang; Youhong Hu

doi:10.1039/C7RA13070H

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Direct C–H functionalization of difluoroboron dipyrromethenes (BODIPYs) at β-position by iodonium salts†

Wenming Ren,‡^a Huaijiang Xiang,‡^b Chengyuan Peng,^a Zulipali Musha,^ac Jingjing Chen,^ac Xin Li,

^b Ruimin Huang*^ac and Youhong Hu

*^ac

Author affiliations

* Corresponding authors

^a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China
E-mail: yhhu@simm.ac.cn, rmhuang@simm.ac.cn

^b College of Pharmaceutical Sciences, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, China

^c University of Chinese Academy of Sciences, 19 Yuquan Road, Beijing 110039, China

Abstract

A copper-catalyzed direct C–H arylation or vinylation of BODIPYs at the β-position by iodonium salts has been developed, which provides facile access to a variety of mono-substituted BODIPY dyes. Interestingly, β-styryl BODIPY compound 9b exhibits apparent cytotoxicity after laser irradiation, which has great potential for photodynamic therapy.

This article is part of the themed collection: Editors’ collection: Photodynamic therapy

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DOI: https://doi.org/10.1039/C7RA13070H
Article type: Paper
Submitted: 05 Dec 2017
Accepted: 27 Jan 2018
First published: 01 Feb 2018
This article is Open Access

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RSC Adv., 2018,8, 5542-5549

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Direct C–H functionalization of difluoroboron dipyrromethenes (BODIPYs) at β-position by iodonium salts

W. Ren, H. Xiang, C. Peng, Z. Musha, J. Chen, X. Li, R. Huang and Y. Hu, RSC Adv., 2018, 8, 5542 DOI: 10.1039/C7RA13070H

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Direct C–H functionalization of difluoroboron dipyrromethenes (BODIPYs) at β-position by iodonium salts†

Abstract

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Direct C–H functionalization of difluoroboron dipyrromethenes (BODIPYs) at β-position by iodonium salts

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