Enantioselective Synthesis of Triarylmethanes Containing Three Different Aryl/Heteroaryl Moieties by Chiral Phosphoric Acids Catalyzed Friedel−Crafts Reactions

An efficient catalytic enantioselective Friedel–Crafts reaction of indoles with in situ‐generated 3‐methide‐3 H ‐pyrroles from pyrrole‐3‐carbinols by a chiral phosphoric acid is developed. A large variety of triarylmethanes bearing two different heteroaryl groups (indole and pyrrole) and a phenyl group are achieved in 14%–98% yields with up to 96% ee. Notably, previously unreported triarylmethanes incorporating three distinct heteroaryl moieties are successfully synthesized using this strategy. This synthetic strategy provides a straightforward and versatile approach to enantioenriched triarylmethanes with structural diversity.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2026-03-12
DOI
https://doi.org/10.1002/adsc.70366
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
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article

Enantioselective Synthesis of Triarylmethanes Containing Three Different Aryl/Heteroaryl Moieties by Chiral Phosphoric Acids Catalyzed Friedel−Crafts Reactions

Luyao Li, Meixing Liu, Zhogwen He, Teck‐Peng Loh et al.
Advanced Synthesis & Catalysis
Synthesis of Indole Derivatives
article

Enantioselective Synthesis of Triarylmethanes Containing Three Different Aryl/Heteroaryl Moieties by Chiral Phosphoric Acids Catalyzed Friedel−Crafts Reactions

Luyao Li, Meixing Liu, Zhogwen He, Teck‐Peng Loh, Yanyan He
article en

Abstract

An efficient catalytic enantioselective Friedel–Crafts reaction of indoles with in situ‐generated 3‐methide‐3 H ‐pyrroles from pyrrole‐3‐carbinols by a chiral phosphoric acid is developed. A large variety of triarylmethanes bearing two different heteroaryl groups (indole and pyrrole) and a phenyl group are achieved in 14%–98% yields with up to 96% ee. Notably, previously unreported triarylmethanes incorporating three distinct heteroaryl moieties are successfully synthesized using this strategy. This synthetic strategy provides a straightforward and versatile approach to enantioenriched triarylmethanes with structural diversity.

Advanced Synthesis & CatalysisVol. 368(6)
Nanyang Technological University (SG), Henan University of Technology (CN)
Openalex Percentile: Top 24%
Synthesis of Indole Derivatives
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