title: Stepwise Polychlorination of 8-Chloro-BODIPY and Regioselective Functionalization of 2,3,5,6,8-Pentachloro-BODIPY.
abstract: 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.
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.
authors.forename: Ning
authors.initials: N
authors.lastname: Zhao
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.
authors.forename: Sunting
authors.initials: S
authors.lastname: Xuan
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.
authors.forename: Frank R
authors.initials: FR
authors.lastname: Fronczek
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.
authors.forename: Kevin M
authors.initials: KM
authors.lastname: Smith
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.
authors.forename: M Graça H
authors.initials: MG
authors.lastname: Vicente
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: C000604177:2,3,5,6,8-pentachloro-BODIPY; C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001372:Aza Compounds; D001896:Boron Compounds; D006843:Hydrocarbons, Chlorinated; D006846:Hydrocarbons, Halogenated