One-Pot Three-Component Coupling of Arylhydrazines with Aryl Aldehydes to Access the Triarylmethane Scaffold

We herein report a one-pot, three-component coupling of arylhydrazine HCl salts with aryl aldehydes to synthesize a triarylmethane scaffold. This reaction proceeds under simple, mild, and practical conditions without the need for an additional Bro̷nsted or Lewis acid additive, accommodating a broad substrate scope with good to excellent yields. Furthermore, this methodology can be scaled up and allows access to a diverse range of triarylmethane derivatives. Mechanistic studies suggest that the in situ formed hydrazone intermediate is essential for the high efficiency and selectivity of this transformation.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-05-08
DOI
https://doi.org/10.1021/acs.joc.5c00082
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
0.00

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article

One-Pot Three-Component Coupling of Arylhydrazines with Aryl Aldehydes to Access the Triarylmethane Scaffold

Yunjiao Wang, Mingxia Liu, Xiaokun Zhai, Yilin Xu et al.
The Journal of Organic Chemistry
Synthesis of Indole Derivatives
article

One-Pot Three-Component Coupling of Arylhydrazines with Aryl Aldehydes to Access the Triarylmethane Scaffold

Yunjiao Wang, Mingxia Liu, Xiaokun Zhai, Yilin Xu, Jin Wang, Shuo Zhang, Dong Wang
article en

Abstract

We herein report a one-pot, three-component coupling of arylhydrazine HCl salts with aryl aldehydes to synthesize a triarylmethane scaffold. This reaction proceeds under simple, mild, and practical conditions without the need for an additional Bro̷nsted or Lewis acid additive, accommodating a broad substrate scope with good to excellent yields. Furthermore, this methodology can be scaled up and allows access to a diverse range of triarylmethane derivatives. Mechanistic studies suggest that the in situ formed hydrazone intermediate is essential for the high efficiency and selectivity of this transformation.

The Journal of Organic ChemistryVol. 90(20)
Shandong Normal University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 93%
Synthesis of Indole Derivatives
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