Synthesis of o-Aminophenols via a Formal Insertion Reaction of Arynes into Hydroxyindolinones.

Journal Article (Journal Article)

A novel approach toward the synthesis of sterically hindered o-aminophenols has been achieved by a formal aryne insertion into hydroxyindolinones. This transformation offers a rapid and efficient entry to diverse o-aminophenol scaffolds under mild transition-metal-free conditions. The reaction involves the addition of hydroxyindolinones to arynes followed by a chemo- and regioselective [1,3]-rearrangement. Furthermore, the reactions of N-hydroxyindoles and arynes were found to provide the C3-aryl indole products via an alternative [3,3]-rearrangement pathway.

Full Text

Duke Authors

Cited Authors

  • Chen, Z; Wang, Q

Published Date

  • December 8, 2015

Published In

Volume / Issue

  • 17 / 24

Start / End Page

  • 6130 - 6133

PubMed ID

  • 26646410

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/acs.orglett.5b03147


  • eng