title: Efficient synthesis and reactions of 1,2-dipyrrolylethynes.
abstract: Various dipyrroles possess important motifs for construction of pyrrole-containing pigments. A series of 1,2-dipyrrolylethynes (4a-d) has been efficiently synthesized using an improved one-pot double Sonagashira coupling from trimethylsilylethyne and various 2-iodopyrroles. The resulting 1,2-dipyrrolylethynes were further transformed into novel indolyl-, ethenyl- and carboranyl-dipyrroles (5-7) using the Larock indole synthesis, stereoselective catalytic hydrogenation, or B(10)H(14). Indolyl-dipyrroles were found to selectively bind fluoride ions using one pyrrolic and the indolyl NHs, whereas the carboranyl- and ethenyl-dipyrroles are potentially valuable precursors for the synthesis of porphyrin isomers and expanded pigments.
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
authors.forename: Hillary K
authors.initials: HK
authors.lastname: Tanui
authors.forename: Erhong
authors.initials: E
authors.lastname: Hao
authors.forename: Moses I
authors.initials: MI
authors.lastname: Ihachi
authors.forename: Frank R
authors.initials: FR
authors.lastname: Fronczek
authors.forename: Kevin M
authors.initials: KM
authors.lastname: Smith
authors.forename: M Graça H
authors.initials: MG
authors.lastname: Vicente