Photoredox Asymmetric Nucleophilic Dearomatization of Indoles with Neutral Radicals

Yueteng Zhang, Peng Ji, Feng Gao, He Huang, Fanxun Zeng, Wei Wang

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


The dearomatization of indoles represents the most efficient approach for accessing highly valued indolines. The inherent nucleophilic reactivity of indoles has dictated indole dearomatization development in both 1e- and 2e- processes. However, the dearomatization of electron-deficient indoles has been challenging. Herein, we introduce a conceptually distinct photoredox-mediated Giese-type transformation strategy, which is generally used for the conjugate addition of radicals to simple α, β-unsaturated systems, for chemoselectively breaking C=C bonds embedded in the aromatic structure. Moreover, highly diastereoselective addition of challenging neutral radicals has been achieved by Oppolzer camphorsultam chiral auxiliary. Structurally diverse amine-functionalized chiral indolines carrying distinct functional and stereochemical diversity are produced from a wide array of amines as radical precursors. Furthermore, the mild, powerful manifold is capable of the late-stage modification of complex natural products and pharmaceuticals. DFT studies are performed to elucidate the observed stereochemical outcomes.

Original languageEnglish (US)
Pages (from-to)998-1007
Number of pages10
JournalACS Catalysis
Issue number2
StatePublished - Jan 15 2021
Externally publishedYes


  • Giese reaction
  • asymmetric dearomatization
  • neutral radical
  • nucleophilic dearomatization
  • photoredox

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)


Dive into the research topics of 'Photoredox Asymmetric Nucleophilic Dearomatization of Indoles with Neutral Radicals'. Together they form a unique fingerprint.

Cite this