Metal‐Catalyzed Regiospecific (4+3) Cyclization of 2‐Indolylmethanols with <i>ortho</i>‐Quinone Methides
Si‐Jia Zhou, Meng Sun, Jing‐Yi Wang, Xian‐Yang Yu, Lu Han, Yu‐Chen Zhang, Feng Shi
Abstract
The first metal‐catalyzed C3‐nucleophilic (4+3) cyclization of 2‐indolylmethanols with stable ortho ‐quinone methides has been established, which constructed indole‐based seven‐membered heterocycles in high yields (70 %‐98 %) with regiospecificity. This reaction has tackled the challenges in exploring the C3‐nucleophilicity of 2‐indolylmethanols, which will contribute to the chemistry of 2‐indolylmethanols, especially to metal‐catalyzed cyclizations of 2‐indolylmethanols. In addition, this approach will provide a useful method for constructing indole‐based seven‐membered heterocycles with high efficiency and regioselectivity.
Topics & Concepts
ChemistryNucleophileRegioselectivityIndole testQuinoneCatalysisMetalCombinatorial chemistryOrganic chemistryMedicinal chemistrySynthesis of Indole DerivativesSulfur-Based Synthesis TechniquesChemical Synthesis and Reactions