ChemInform Abstract: Efficient Synthesis of Carbazoles via PtCl 2 -Catalyzed RT Cyclization of 1-(Indol-2-yl)-2,3-allenols: Scope and Mechanism.

ArticleinOrganic & Biomolecular Chemistry 10(10):2164-73 · March 2012with12 Reads
Impact Factor: 3.56 · DOI: 10.1039/c1ob06474f · Source: PubMed


    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.