Issue 14, 2021
From the journal:

Chemical Communications

Highly regioselective palladium-catalyzed domino reaction for post-functionalization of BODIPY†

Sisi Wang, ORCID logo a   Zhaoli Wang,a   Hu Gao,a   Liang Jiang,a   Hui Liu,a   Fan Wu, ORCID logo a   Yue Zhao, ORCID logo a   Kin Shing Chan ORCID logo a  and  Zhen Shen ORCID logo *a  

* Corresponding authors

a State Key Laboratory of Coordination Chemistry, Collaborative Innovation Center of Advanced Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210046, P. R. China
E-mail: zshen@nju.edu.cn

Abstract

A series of benzo[a]-fused BODIPYs and the corresponding isomeric naphthyl-BODIPYs have been synthesized through a facile one-pot palladium-catalyzed domino reaction of BODIPY precursors (2-bromo-BODIPYs) with diarylethynes, via “cis, cis” and “trans, cis” addition transition states with alkynes, respectively. This reaction exhibits unprecedentedly complete cyclization regioselectivity to the a-position of the BODIPY over the b-one, and the resulting products can be effectively regulated by the substituent choice on the diarylethynes.

Graphical abstract: Highly regioselective palladium-catalyzed domino reaction for post-functionalization of BODIPY

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Article information

DOI
https://doi.org/10.1039/D0CC08163A
Article type
Communication
Submitted
16 Dec 2020
Accepted
31 Dec 2020
First published
04 Jan 2021

Chem. Commun., 2021,57, 1758-1761

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Highly regioselective palladium-catalyzed domino reaction for post-functionalization of BODIPY

S. Wang, Z. Wang, H. Gao, L. Jiang, H. Liu, F. Wu, Y. Zhao, K. S. Chan and Z. Shen, Chem. Commun., 2021, 57, 1758 DOI: 10.1039/D0CC08163A

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