Copper-Catalyzed Asymmetric Reductive Coupling of Vinyl <i>N</i> -Heteroarenes with <i>para</i> -Quinone Methides

Chiral 1,1,2-triarylethanes represent highly desirable synthetic targets in medicinal chemistry. Herein, we describe a copper-catalyzed asymmetric reductive coupling strategy, wherein vinyl <i>N</i>-heteroarenes are coupled with <i>para</i>-quinone methides (<i>p</i>-QMs) to afford chiral 1,1,2-triarylethanes containing <i>N</i>-heteroarene moieties in 60-99% yields, with enantioselectivities of up to 94% ee and diastereoselectivities of 2:1 to >20:1 dr. This modular protocol features low-cost catalysts, facilely prepared substrates, and good control of stereoselectivity.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-25
DOI
https://doi.org/10.1021/acs.joc.5c02834
Citations
1
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
22.95
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article

Copper-Catalyzed Asymmetric Reductive Coupling of Vinyl N -Heteroarenes with para -Quinone Methides

Chun‐An Fan, Xiang Zhen, Xian‐Tao An, Le-Le Meng et al.
1 citations
The Journal of Organic Chemistry
Synthesis of Indole Derivatives
22.95
article

Copper-Catalyzed Asymmetric Reductive Coupling of Vinyl N -Heteroarenes with para -Quinone Methides

Chun‐An Fan, Xiang Zhen, Xian‐Tao An, Le-Le Meng, Xin Zhao, Qi-Qiong Yang, Jing-Rui Xu, Bo Chen
article en
1 citations

Abstract

Chiral 1,1,2-triarylethanes represent highly desirable synthetic targets in medicinal chemistry. Herein, we describe a copper-catalyzed asymmetric reductive coupling strategy, wherein vinyl <i>N</i>-heteroarenes are coupled with <i>para</i>-quinone methides (<i>p</i>-QMs) to afford chiral 1,1,2-triarylethanes containing <i>N</i>-heteroarene moieties in 60-99% yields, with enantioselectivities of up to 94% ee and diastereoselectivities of 2:1 to >20:1 dr. This modular protocol features low-cost catalysts, facilely prepared substrates, and good control of stereoselectivity.

The Journal of Organic ChemistryVol. 91(5)
China West Normal University (CN), Chemical Synthesis Lab (SG), Lanzhou University (CN)
Openalex Percentile: Top 2%
Synthesis of Indole Derivatives
22.95
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Copper-Catalyzed Asymmetric Reductive Coupling of Vinyl <i>N</i> -Heteroarenes with <i>para</i> -Quinone Methides — Chun‐An Fan, Xiang Zhen, et al. · The Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS