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 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.

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1,2-二吡咯乙炔的高效合成和反应

各种二吡咯具有构建含吡咯颜料的重要基序。使用改进的一锅双 Sonagashira 偶联法，由三甲基甲硅烷基乙炔和各种 2-碘吡咯高效合成了一系列 1,2-二吡咯乙炔 (4a–d)。使用 Larock 吲哚合成、立体选择性催化氢化或 B，将所得 1,2-二吡咯乙炔进一步转化为新型吲哚基、乙烯基和碳硼烷基二吡咯 (5–7)10H14。吲哚基二吡咯被发现使用一种吡咯和吲哚基NH选择性地结合氟离子，而碳硼烷基和乙烯基二吡咯是用于合成卟啉异构体和膨胀颜料的潜在有价值的前体。