通过卡宾转移反应的金催化σ-迁移重排反应。
Gold-Catalyzed Sigmatropic Rearrangement Reactions via Carbene Transfer Reactions.
作者信息
He Feifei, Jana Sripati, Koenigs Rene M
机构信息
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, D-52074 Aachen, Germany.
出版信息
J Org Chem. 2020 Sep 18;85(18):11882-11891. doi: 10.1021/acs.joc.0c01678. Epub 2020 Sep 8.
Sigmatropic rearrangements are an important fundamental toolbox in organic synthesis to access complex molecular fragments. Yet, the rearrangement reactions of onium ylides via gold catalyzed carbene transfer reactions are relatively unexplored. Herein, we describe a gold-catalyzed sigmatropic rearrangement of sulfonium and selenium ylides (39 examples, up to 99% yield). Furthermore, we report on the limitations of sigmatropic rearrangement reactions of aryl allyl anilines, which deliver exclusively C-H functionalized products.
[3,3] - 迁移重排反应是有机合成中用于构建复杂分子片段的重要基础工具。然而，通过金催化的卡宾转移反应实现的鎓叶立德的重排反应相对较少被研究。在此，我们描述了一种金催化的硫鎓叶立德和硒鎓叶立德的[3,3] - 迁移重排反应（39个实例，产率高达99%）。此外，我们报道了芳基烯丙基苯胺的[3,3] - 迁移重排反应的局限性，该反应仅生成C - H官能化产物。
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