School of Pharmacy, Yancheng Teachers University, Yancheng 224007, China.
Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China.
Org Lett. 2022 Jul 15;24(27):4919-4924. doi: 10.1021/acs.orglett.2c01800. Epub 2022 Jun 30.
An efficient Sonogashira coupling of a heterocyclic phosphonium salt with a terminal alkyne via C-P bond cleavage was developed. The reactions proceeded smoothly in the presence of palladium catalyst, copper(I) iodide, and ,-diisopropylethylamine (DIPEA) in -methyl-2-pyrrolidone (NMP) at 100 °C for 12 h, producing the corresponding alkynyl-substituted pyridine, quinoline, pyrazine, and quinoxaline in moderate to good yields with wide substrate scope and broad functional group tolerance. In addition, gram-scale synthesis could also be achieved, and the reaction could be applied to the functionalization of alkyne-containing complex molecules derived from sugars and pharmaceutical and naturally occurring products (e.g., estrone, d-galactopyranose, menthol, and ibuprofen).
开发了一种通过 C-P 键断裂将杂环膦盐与末端炔烃高效偶联的 Sonogashira 反应。在 100°C 下，钯催化剂、碘化亚铜和,-二异丙基乙胺（DIPEA）在 N-甲基-2-吡咯烷酮（NMP）中反应 12 小时，该反应能以中等至良好的收率、较宽的底物范围和广泛的官能团耐受性得到相应的炔基取代吡啶、喹啉、吡嗪和喹喔啉。此外，还可以进行克级规模的合成，并且该反应可以应用于糖和药物及天然产物（如雌酮、D-吡喃半乳糖、薄荷醇和布洛芬）衍生的含炔烃的复杂分子的功能化。
