Related Experiment Video
Updated: Jun 13, 2026
![[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[(DPEPhos)(bcp)Cu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Unsymmetric 2,3- and 3,6-Disubstituted BODIPYs: Regioselective Synthesis, Reactivity, and Photophysical Properties
Yuqi Xie1, Xiaoting Liu1, Huiquan Zuo2
1School of Pharmacy, Anhui University of Chinese Medicine, Hefei 230012, China.
None:
A series of 2,3- or 3,6-halogenated BODIPYs were synthesized from readily available 2- or 3-monohalogenated BODIPYs via highly regioselective electrophilic substitution and α-chlorination, affording good yields and broad substrate compatibility. These halogenated BODIPYs serve as versatile platforms for postfunctionalization via Pd-catalyzed Stille and Suzuki couplings, offering access to novel 2,3- or 3,6-disubstituted BODIPY derivatives that were difficult to obtain previously. The compounds exhibit red-shifted absorption and emission, including a near-infrared lipid droplet imaging probe with low cytotoxicity.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Related Concept Videos
Thermal and Photochemical Electrocyclic Reactions: Overview
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Woodward–Hoffmann Selection Rules and Microscopic Reversibility
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Cycloaddition Reactions: MO Requirements for Photochemical Activation