Regioselective Halogenation of BOPPY Fluorophores and Subsequent Diversification via Cross-Coupling and Aromatic Nucleophilic Substitution Strategies.

Sebastian O Oloo, Petia Bobadova-Parvanova, Alexis A Lueders, Mina Kim, Frank R Fronczek, Kevin M Smith, Maria da Graça H Vicente

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Article in The Journal of organic chemistry, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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7 authors.

Sebastian O OlooDepartment of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.

Petia Bobadova-ParvanovaDepartment of Chemistry and Fermentation Sciences, Appalachian State University, Boone, North Carolina 28608, United States.ORCID 0000-0002-1965-419X

Alexis A LuedersDepartment of Chemistry and Fermentation Sciences, Appalachian State University, Boone, North Carolina 28608, United States.

Mina KimDepartment of Chemistry and Fermentation Sciences, Appalachian State University, Boone, North Carolina 28608, United States.

Frank R FronczekDepartment of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.ORCID 0000-0001-5544-2779

Kevin M SmithDepartment of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.ORCID 0000-0002-6736-4779

Maria da Graça H VicenteDepartment of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, United States.ORCID 0000-0002-4429-7868

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6 · The paper itself

Abstract

The regioselective mono- and tribromination of a BOPPY dye followed by its reactivity under Pd-catalyzed cross-coupling and nucleophilic substitution reactions are reported. The brominated BOPPYs undergo Pd(0)-catalyzed cross-couplings with a variety of boronic acids and organotin reagents to give the corresponding products in good-to-excellent yields. Nucleophilic aromatic substitutions occur both on the mono- and tribromo-BOPPYs. The reactivity order of the latter is C3-Br > C1-Br > C2-Br, while in the cross-coupling reactions using Pd(PPh

Identifiers

PMID41805343

DOI10.1021/acs.joc.5c03121

PMCPMC13010255

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