Cu(I)-catalysed chemo-, regio-, and stereoselective radical 1,2-carboalkynylation with two different terminal alkynes

Transition-metal-catalysed asymmetric multicomponent reactions with two similar substrates often suffer from the lack of strategies to control the chemo-, regio-, and stereoselectivity of these substrates due to the close similarity in the chemical structures and properties of each reagent. Here, we describe a Cu(I)-catalysed asymmetric radical 1,2-carboalkynylation of two different terminal alkynes and alkyl halides with high chemo-, regio-, and stereoselectivity by using sterically bulky chiral tridentate anionic N,N,P-ligands and modulating alkynes with different electronic properties to circumvent above-mentioned challenges. This method features good substrate scope, high functional group tolerance of two different terminal alkynes, and diverse alkyl halides, providing universal access to a series of useful axially chiral 1,3-enyne building blocks.

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Publication Details

Journal
Nature Communications
Published
2025-05-27
DOI
https://doi.org/10.1038/s41467-025-60012-z
Citations
6
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
5.62

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article

Cu(I)-catalysed chemo-, regio-, and stereoselective radical 1,2-carboalkynylation with two different terminal alkynes

Jun-Bin Tang, Zhong‐Liang Li, Yong‐Feng Cheng, Song Qiao et al.
6 citations
Nature Communications
Catalytic C–H Functionalization Methods
5.62
article

Cu(I)-catalysed chemo-, regio-, and stereoselective radical 1,2-carboalkynylation with two different terminal alkynes

Jun-Bin Tang, Zhong‐Liang Li, Yong‐Feng Cheng, Song Qiao, Liwen Fan, Jun-Qian Bian, Qiang‐Shuai Gu, Jiajia Fu, Qin Li, Yufeng Zhang, Xin‐Yuan Liu, Peng Yu, Pengfei Wang
article en
6 citations

Abstract

Transition-metal-catalysed asymmetric multicomponent reactions with two similar substrates often suffer from the lack of strategies to control the chemo-, regio-, and stereoselectivity of these substrates due to the close similarity in the chemical structures and properties of each reagent. Here, we describe a Cu(I)-catalysed asymmetric radical 1,2-carboalkynylation of two different terminal alkynes and alkyl halides with high chemo-, regio-, and stereoselectivity by using sterically bulky chiral tridentate anionic N,N,P-ligands and modulating alkynes with different electronic properties to circumvent above-mentioned challenges. This method features good substrate scope, high functional group tolerance of two different terminal alkynes, and diverse alkyl halides, providing universal access to a series of useful axially chiral 1,3-enyne building blocks.

Nature CommunicationsVol. 16(1)
Dongguan University of Technology (CN), Southern University of Science and Technology (CN), Centre of Excellence for Advanced Materials (CN), Institute for Advanced Study (DE)
National Natural Science Foundation of China, Southern University of Science and Technology
Clean water and sanitation
Openalex Percentile: Top 4%
Catalytic C–H Functionalization Methods
5.62
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