Enantioselective Synthesis of Triarylmethanes via One-Pot Asymmetric Gold(I)/Rhodium(I) Relay Catalysis

The asymmetric synthesis of chiral triarylmethanes is highly challenging due to the difficulty in constructing a stereocenter at the central carbon, which is surrounded by three aryl groups and requires precise control over substituent spatial arrangement. Herein, we report a one-pot asymmetric gold(I)/rhodium(I) relay catalysis strategy for synthesizing chiral triarylmethanes. This bimetallic-catalyzed cascade reaction, involving intramolecular cyclization and enantioselective conjugate arylation, proceeds under mild conditions with high yields and enantioselectivities for a wide range of enynamides and arylboronic acids. The method enables efficient access to chiral triarylmethanes featuring a furan unit, including those with two or three heteroaryl groups. The synthetic utility of this approach is further demonstrated by diversifying products through transformations of the furan unit.

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Publication Details

Journal
ACS Catalysis
Published
2025-07-16
DOI
https://doi.org/10.1021/acscatal.5c03050
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
0.00

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article

Enantioselective Synthesis of Triarylmethanes via One-Pot Asymmetric Gold(I)/Rhodium(I) Relay Catalysis

Ming‐Hua Xu, Bo Kang
ACS Catalysis
Synthesis of Indole Derivatives
article

Enantioselective Synthesis of Triarylmethanes via One-Pot Asymmetric Gold(I)/Rhodium(I) Relay Catalysis

Ming‐Hua Xu, Bo Kang
article en

Abstract

The asymmetric synthesis of chiral triarylmethanes is highly challenging due to the difficulty in constructing a stereocenter at the central carbon, which is surrounded by three aryl groups and requires precise control over substituent spatial arrangement. Herein, we report a one-pot asymmetric gold(I)/rhodium(I) relay catalysis strategy for synthesizing chiral triarylmethanes. This bimetallic-catalyzed cascade reaction, involving intramolecular cyclization and enantioselective conjugate arylation, proceeds under mild conditions with high yields and enantioselectivities for a wide range of enynamides and arylboronic acids. The method enables efficient access to chiral triarylmethanes featuring a furan unit, including those with two or three heteroaryl groups. The synthetic utility of this approach is further demonstrated by diversifying products through transformations of the furan unit.

ACS Catalysis
Southern University of Science and Technology (CN), Henan Normal University (CN)
National Natural Science Foundation of China, Guangdong Science and Technology Department, Science, Technology and Innovation Commission of Shenzhen Municipality, Guangdong Provincial Key Laboratory Of Catalysis
Openalex Percentile: Top 87%
Synthesis of Indole Derivatives
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