Asymmetric Nickel-Catalyzed Denitrogenative Transannulation to Construct Axially Chiral C–N Atropisomers

Here, we report an enantioselective nickel-catalyzed transannulation reaction through a denitrogenative strategy for the synthesis of new atropisomers under mild conditions. A series of axially chiral atropisomers bearing a chiral C-N bond were achieved with excellent enantioselectivities and regioselectivities. Moreover, a broad range of alkynes and 1,2,3-benzotriazinones were well tolerated by this method. The possible mechanism further reveals the role of nickel and the enantioselectivity control.

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Publication Details

Journal
Organic Letters
Published
2025-08-04
DOI
https://doi.org/10.1021/acs.orglett.5c02872
Citations
2
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
Field-Weighted Citation Impact
1.87

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article

Asymmetric Nickel-Catalyzed Denitrogenative Transannulation to Construct Axially Chiral C–N Atropisomers

Yanjian Wan, Yafei Guo, Yu Chen, Wenxing Liu et al.
2 citations
Organic Letters
Axial and Atropisomeric Chirality Synthesis
1.87
article

Asymmetric Nickel-Catalyzed Denitrogenative Transannulation to Construct Axially Chiral C–N Atropisomers

Yanjian Wan, Yafei Guo, Yu Chen, Wenxing Liu, Jiuling Li, Liangrui Xiao
article en
2 citations

Abstract

Here, we report an enantioselective nickel-catalyzed transannulation reaction through a denitrogenative strategy for the synthesis of new atropisomers under mild conditions. A series of axially chiral atropisomers bearing a chiral C-N bond were achieved with excellent enantioselectivities and regioselectivities. Moreover, a broad range of alkynes and 1,2,3-benzotriazinones were well tolerated by this method. The possible mechanism further reveals the role of nickel and the enantioselectivity control.

Organic LettersVol. 27(32)
Minzu University of China (CN)
National Natural Science Foundation of China, Yunnan Provincial Department of Education
Openalex Percentile: Top 14%
Axial and Atropisomeric Chirality Synthesis
1.87
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Asymmetric Nickel-Catalyzed Denitrogenative Transannulation to Construct Axially Chiral C–N Atropisomers — Yanjian Wan, Yafei Guo, et al. · Organic Letters (2025) | TGRS Research Map | TGRS