Stepwise Polychlorination of 8‑Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY

An effective, stepwise methodology for polychlorination of BODIPY using trichloroisocyanuric acid (TCCA) in acetic acid was developed. In this way, selectively substituted di-, tri-, tetra-, and pentachloro-BODIPYs 2–5 were prepared. The pentachloro-BODIPY is shown to undergo regioselective Pd(0)-ca...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-08, Vol.80 (16), p.8377-8383
Main Authors: Zhao, Ning, Xuan, Sunting, Fronczek, Frank R, Smith, Kevin M, Vicente, M. Graça H
Format: Article
Language:English
Subjects:
Aza Compounds - chemistry
Boron Compounds - chemistry
Catalysis
Crystallography, X-Ray
Hydrocarbons, Chlorinated - chemical synthesis
Hydrocarbons, Chlorinated - chemistry
Hydrocarbons, Halogenated - chemistry
Molecular Structure
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Summary:An effective, stepwise methodology for polychlorination of BODIPY using trichloroisocyanuric acid (TCCA) in acetic acid was developed. In this way, selectively substituted di-, tri-, tetra-, and pentachloro-BODIPYs 2–5 were prepared. The pentachloro-BODIPY is shown to undergo regioselective Pd(0)-catalyzed Stille and Suzuki coupling reactions, first at the 8-position followed by the 3,5- and then the 2,6-positions; nucleophilic substitution reactions occur first at the 8- followed by the 3,5-positions, while the 2,6 are unreactive.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01147