State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P.R. China.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, P.R. China.
J Org Chem. 2021 Dec 3;86(23):16977-16991. doi: 10.1021/acs.joc.1c02117. Epub 2021 Nov 18.
A novel method for P-involved heterocycle ring-closing-ring-opening rearrangement (HRR) via the Heck reaction is disclosed. The approach enables direct installation of a phosphorus-containing aryl group onto the C2 position of indole. This new rearrangement directly transforms easily prepared indole derivatives into indolyl-derived phosphonates and phosphinic acids with high yields, and many of the products are difficult to obtain by using established methods. This new HRR reaction provides an extremely simple and step-economic method to induce C-C bond formation and P-N bond cleavage for the synthesis of a variety of indolyl-type ligands.
本文公开了一种通过 Heck 反应实现磷参与的杂环闭环-开环重排（HRR）的新方法。该方法能够将含磷芳基直接安装到吲哚的 C2 位置上。这种新的重排反应能够以高产率直接将易于制备的吲哚衍生物转化为吲哚衍生的膦酸酯和次膦酸，并且许多产物都难以通过现有的方法获得。这种新的 HRR 反应为合成各种吲哚型配体提供了一种极其简单和经济的方法，可诱导 C-C 键形成和 P-N 键断裂。
