PtCl4-catalyzed skeleton rearrangement-cyclization of tertiary indolyl-3-alkynols

Jing Zhou; Youai Qiu; Junzhao Li; Chunling Fu; Xue Zhang; Shengming Ma

doi:10.1039/c7cc00352h

PtCl₄-catalyzed skeleton rearrangement-cyclization of tertiary indolyl-3-alkynols

Chem Commun (Camb). 2017 Apr 25;53(34):4722-4725. doi: 10.1039/c7cc00352h.

Authors

Jing Zhou¹, Youai Qiu, Junzhao Li, Chunling Fu, Xue Zhang, Shengming Ma

Affiliation

¹ Laboratory of Molecular Recognition and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, Zhejiang, People's Republic of China. masm@sioc.ac.cn.

PMID: 28401967
DOI: 10.1039/c7cc00352h

Abstract

An unexpected PtCl₄-catalyzed cyclization reaction of tertiary indol-2-yl-3-alkynols occurred smoothly in toluene to form various poly-substituted carbazole derivatives efficiently. A possible mechanism involving the formation of a spiro-tricyclic intermediate via indole C-2 attack, highly selective ring expansion and then 1,2-migration has been proposed for the formation of carbazoles.