Tandem Oxidative Nucleophilic Hydrogen Substitution/B–O Cyclization Enables Chiral Near-Infrared N,O,B-Chelated BODIPYs

Organic Letters 2026

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Authors: Hua Wang, Yuting Zhang, Wenxin Gu, Qinghua Wu, Y U E J I He, Zhengxin Kang, L Wang, Hui Li, Xing Guo, Huiquan Zuo, Lijuan Jiao, Erhong Hao
DOI: 10.1021/acs.orglett.6c02925
Cited by: 1
References: 47

Abstract

We report a mild, modular tandem strategy that transforms readily available B-substituted BODIPYs into a new class of N,O,B-chelated BODIPYs with intense near-infrared absorption/emission. The key transformation involves oxidative nucleophilic substitution of α-hydrogens (ONSH) followed by intramolecular B-O cyclization, operating with diverse ketones (acetophenones, indanones, tetralones, acenaphthenone). X-ray crystallography reveals a tetrahedral boron center that is inherently stereogenic. Chiral resolution by HPLC and circular dichroism spectroscopy confirm the optical activity of the enantiomers.

Fields of Study & Subjects

Luminescence and Fluorescent Materials Organoboron and organosilicon chemistry Synthesis and Properties of Aromatic Compounds

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
31
Pages
10128–10133
Publication date
27 July 2026
Language
EN