title: Synthesis of SF5-Substituted Tetrapyrroles, Metalloporphyrins, BODIPYs, and Their Dipyrrane Precursors.
abstract: The synthesis of novel pentafluorosulfanyl (SF5)-substituted A4-type porphyrins, their corresponding Zn(II)- and Pd(II)-metal complexes, A3-, A2B- and AB2-type corroles, BODIPYs, and their dipyrrane precursors was studied utilizing commercially available SF5-substituted aryl aldehydes. In addition, the functionalization of SF5-substituted tetrapyrroles was investigated by applying the concept of the nucleophilic aromatic substitution (S(N)Ar) with alcohols and sodium azide onto the pentafluorophenyl moiety of a trans-A2B2-porphyrin and two corrole derivatives with a mixed substitution pattern involving the SF5 group. This allows a fine-tuning of the properties of these macrocycles through a selective and mild introduction of functional groups, giving access to multifunctionalized SF5-substituted porphyrinoids. As an example, one functionalized corrole was further reacted with an azido-substituted BODIPY via the copper(I)-catalyzed 1,3-dipolar cycloaddition yielding the first corrole-BODIPY heterodimer involving the pentafluorosulfanyl group.
authors: †Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany.|‡Biolitec Research GmbH, Otto-Schott-Strasse 15, 07745 Jena, Germany.
authors: Hartwig R A
authors: HR
authors: Golf
authors: †Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany.
authors: Hans-Ulrich
authors: HU
authors: Reissig
authors: †Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany.|‡Biolitec Research GmbH, Otto-Schott-Strasse 15, 07745 Jena, Germany.
authors: Arno
authors: A
authors: Wiehe
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D056831:Coordination Complexes / Q000737:chemistry; D061565:Cycloaddition Reaction; D008665:Metalloporphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*; D045725:Tetrapyrroles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D056831:Coordination Complexes; D008665:Metalloporphyrins; D011714:Pyrans; D013457:Sulfur Compounds; D045725:Tetrapyrroles; D010165:Palladium