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April 27, 2026ACS Catalysis0 citations

Chiral η 6 -Benzene Ruthenium(II)-Catalyzed Asymmetric C−H Activation/Annulation To Construct C−N Axially Chiral Indoles

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JJJunlian JiYWYì Wáng

Key Points

  • The aim is to explore asymmetric C−H activation using chiral benzene ruthenium catalysts to synthesize axially chiral indoles.
  • C−H activation/annulation of anilines with alkynes using a chiral BenRuII complex derived from (S)-H8−BINOL.
  • Yield and enantiomeric excess (ee) were measured, achieving up to 97% yield and 98% ee.
  • Mechanistic investigations included H/D exchange experiments and kinetic isotope effect studies.
  • Up to 97% yield and 98% ee of various C−N axially chiral indoles were obtained.
  • A metallacyclic intermediate was isolated and characterized as catalytically active.
  • Kinetic isotope effect studies provided insights into the reaction mechanism.

Abstract

Asymmetric C−H activation enabled by chiral η6-benzene ruthenium (BenRu) catalysts is an emerging research field. Herein, we report the asymmetric C−H activation/annulation of anilines with alkynes catalyzed by a chiral BenRuᴵᴵ complex derived from (S)-H8−BINOL. A variety of C−N axially chiral indoles were obtained (up to 97% yield and 98% ee). Mechanistic investigations, including H/D exchange experiments and kinetic isotope effect studies, were conducted. A metallacyclic intermediate was isolated, characterized, and shown to be catalytically active in the model reaction.

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Cite This Study

Ji et al. (2026) studied this question.

synapsesocial.com/papers/69eefcf4fede9185760d3b47https://doi.org/10.1021/acscatal.6c01461
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