Organophotocatalytic dearomatization of indoles, pyrroles and benzo(thio)furans via a Giese-type transformation

Yueteng Zhang, Peng Ji, Feng Gao, Yue Dong, He Huang, Changqing Wang, Ziyuan Zhou, Wei Wang

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

Accessing fascinating organic and biological significant indolines via dearomatization of indoles represents one of the most efficient approaches. However, it has been difficult for the dearomatization of the electron deficient indoles. Here we report the studies leading to developing a photoredox mediated Giese-type transformation strategy for the dearomatization of the indoles. The reaction has been implemented for chemoselectively breaking indolyl C=C bonds embedded in the aromatic system. The synthetic power of this strategy has been demonstrated by using structurally diverse indoles bearing common electron-withdrawing groups including (thio)ester, amide, ketone, nitrile and even aromatics at either C2 or C3 positions and ubiquitous carboxylic acids as radical coupling partner with high trans-stereoselectivity (>20:1 dr). This manifold can also be applied to other aromatic heterocycles including pyrroles, benzofurans and benzothiophenes. Furthermore, enantioselective dearomatization of indoles has been achieved by a chiral camphorsultam auxiliary with high diastereoselectivity.

Original languageEnglish (US)
Article number20
JournalCommunications Chemistry
Volume4
Issue number1
DOIs
StatePublished - Dec 2021

ASJC Scopus subject areas

  • General Chemistry
  • Materials Chemistry
  • Biochemistry
  • Environmental Chemistry

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