Document Type
Article
Publication Date
8-21-2015
Abstract
© 2015 American Chemical Society. 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.
Publication Source (Journal or Book title)
Journal of Organic Chemistry
First Page
8377
Last Page
8383
Recommended Citation
Zhao, N., Xuan, S., Fronczek, F., Smith, K., & Vicente, M. (2015). Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY. Journal of Organic Chemistry, 80 (16), 8377-8383. https://doi.org/10.1021/acs.joc.5b01147