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Iodoindenes: Synthesis and application to cross-coupling
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2020-09-12 , DOI: 10.1016/j.tetlet.2020.152427
A. Hasan Howlader , Keili Diaz , Alexander M. Mebel , Ralf I. Kaiser , Stanislaw F. Wnuk

An expeditious synthesis of 5-, 6-, and 7-iodoindenes from the corresponding aminoindan-1-ones in more than 70% yield employing readily available precursors and ubiquitous reagents is reported. The 4-iodoindene has been prepared analogously in 40% overall yield. A three-step sequence involves diazotization-iodination of aminoindan-1-one followed by the reduction and dehydration. The iodoindenes serve as effective substrates for the regioselective Stille coupling with vinyl stannanes but isomeric mixtures are produced during Sonogashira coupling with alkynes in the presence of triethylamine.



中文翻译:

碘茚:合成及其在交叉偶联中的应用

据报道,使用容易获得的前体和普遍存在的试剂,可以以超过70%的产率从相应的氨基茚满-1-酮快速合成5-,6-和7-碘茚。类似地,以40%的总产率制备4-碘茚。一个三步骤的序列涉及氨基茚满-1-一的重氮化-碘化,然后进行还原和脱水。碘代茚是与乙烯基锡烷进行区域选择性Stille偶联的有效底物,但在三乙胺存在下,在Sonogashira与炔烃偶联的过程中产生了异构体混合物。

更新日期:2020-10-06
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