Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People's Republic of China.
Org Biomol Chem. 2012 Mar 14;10(10):2164-73. doi: 10.1039/c1ob06474f. Epub 2012 Feb 2.
A detailed study on the scope of the efficient PtCl(2)-catalyzed synthesis of carbazoles from 1-(indol-2-yl)-2,3-allenols is described. Through isotopic labeling experiments, it is confirmed that the reaction proceeds through a unique metal carbene intermediate, which undergoes subsequent highly selective 1,2-hydrogen migration to afford carbazoles. The reaction shows wide scope and allows the introduction of a variety of different substituents at different positions on the carbazole due to the substituent-loading capability of both indole and the allene moiety.
详细研究了高效 PtCl(2)-催化的 1-(吲哚-2-基)-2,3-烯丙醇合成咔唑的范围。通过同位素标记实验，证实反应通过独特的金属卡宾中间体进行，该中间体随后进行高度选择性的 1,2-氢迁移，得到咔唑。该反应具有广泛的范围，并允许在咔唑的不同位置引入各种不同的取代基，这是由于吲哚和烯丙基部分的取代基负载能力。
