Document Type
Article
Publication Date
1-1-2011
Abstract
Various dipyrroles possess important motifs for construction of pyrrole-containing pigments. A series of 1,2-dipyrrolylethynes (4ad) 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 (57) using the Larock indole synthesis, stereoselective catalytic hydrogenation, or B10H14. 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. © 2011 World Scientific Publishing Company.
Publication Source (Journal or Book title)
Journal of Porphyrins and Phthalocyanines
First Page
412
Last Page
420
Recommended Citation
Tanui, H., Hao, E., Ihachi, M., Fronczek, F., Smith, K., & Vicente, M. (2011). Efficient synthesis and reactions of 1,2-dipyrrolylethynes. Journal of Porphyrins and Phthalocyanines, 15 (5-6), 412-420. https://doi.org/10.1142/S1088424611003331
