Highly regioselective α-formylation and α-acylation of BODIPY dyes via tandem cross-dehydrogenative coupling with in situ deprotection

Fan Lv; Yang Yu; Erhong Hao; Changjiang Yu; Hua Wang; Noёl Boens; Lijuan Jiao

doi:10.1039/C9OB00927B

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Highly regioselective α-formylation and α-acylation of BODIPY dyes via tandem cross-dehydrogenative coupling with in situ deprotection†

Fan Lv,^a Yang Yu,^a Erhong Hao,

*^a Changjiang Yu,

^a Hua Wang,^a Noёl Boens*^b and Lijuan Jiao

*^a

Author affiliations

* Corresponding authors

^a The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, China
E-mail: haoehong@ahnu.edu.cn, jiao421@ahnu.edu.cn

^b Department of Chemistry, KU Leuven (Katholieke Universiteit Leuven), Celestijnenlaan 200f, 3001 Leuven, Belgium
E-mail: noel.boens@kuleuven.be

Abstract

A metal-free C–H formylation and acylation of BODIPY dyes using a variety of dioxolane derivatives as aldehyde equivalents is reported, providing a postfunctionalization method for controllable synthesis of BODIPYs with carbonyl groups at 3,5-positions via a radical process. The photophysical properties of resultant dyes from this efficient one-pot, chemo- and site-selective transformation have been studied.

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

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DOI: https://doi.org/10.1039/C9OB00927B
Article type: Paper
Submitted: 24 Apr 2019
Accepted: 02 May 2019
First published: 03 May 2019

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Org. Biomol. Chem., 2019,17, 5121-5128

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Highly regioselective α-formylation and α-acylation of BODIPY dyes via tandem cross-dehydrogenative coupling with in situ deprotection

F. Lv, Y. Yu, E. Hao, C. Yu, H. Wang, N. Boens and L. Jiao, Org. Biomol. Chem., 2019, 17, 5121 DOI: 10.1039/C9OB00927B

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Organic & Biomolecular Chemistry

Highly regioselective α-formylation and α-acylation of BODIPY dyes via tandem cross-dehydrogenative coupling with in situ deprotection†

Abstract

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Highly regioselective α-formylation and α-acylation of BODIPY dyes via tandem cross-dehydrogenative coupling with in situ deprotection

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