Copper‐Catalyzed Desymmetric Alkyne–Azide Cycloaddition to Access Axially Chiral Biaryls

Abstract Axially chiral biaryls are an important class of structural units widely used in natural product synthesis, drug design, and as ligands for asymmetric catalysis. Although significant progress has been made in the synthesis of axially chiral biaryls, some of them are still limited to narrow substrate ranges, low efficiency, and moderate stereocontrol. Herein, we describe a highly efficient route to prepare atropisomeric biaryls with triazole and alkyne modules through the desymmetrization of prochiral dialkynyl diaryls utilizing chiral cyclobutyl‐bridge box ligands in conjunction with copper salts. The process has mild conditions, good functional‐group tolerance, and can obtain a wide array of valuable axially chiral biaryl derivatives with good to excellent yields and enantioselectivities.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-03-07
DOI
https://doi.org/10.1002/ejoc.202500041
Citations
1
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
Field-Weighted Citation Impact
0.94

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article

Copper‐Catalyzed Desymmetric Alkyne–Azide Cycloaddition to Access Axially Chiral Biaryls

Meng‐Die Li, Tao‐Yan Lin, Bing Liu, Ruixue Liu et al.
1 citations
European Journal of Organic Chemistry
Axial and Atropisomeric Chirality Synthesis
0.94
article

Copper‐Catalyzed Desymmetric Alkyne–Azide Cycloaddition to Access Axially Chiral Biaryls

Meng‐Die Li, Tao‐Yan Lin, Bing Liu, Ruixue Liu, Yu Tian
article en
1 citations

Abstract

Abstract Axially chiral biaryls are an important class of structural units widely used in natural product synthesis, drug design, and as ligands for asymmetric catalysis. Although significant progress has been made in the synthesis of axially chiral biaryls, some of them are still limited to narrow substrate ranges, low efficiency, and moderate stereocontrol. Herein, we describe a highly efficient route to prepare atropisomeric biaryls with triazole and alkyne modules through the desymmetrization of prochiral dialkynyl diaryls utilizing chiral cyclobutyl‐bridge box ligands in conjunction with copper salts. The process has mild conditions, good functional‐group tolerance, and can obtain a wide array of valuable axially chiral biaryl derivatives with good to excellent yields and enantioselectivities.

European Journal of Organic ChemistryVol. 28(17)
Huaibei Normal University (CN), Shanghai University of Sport (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 28%
Axial and Atropisomeric Chirality Synthesis
0.94
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