Palladium-Catalyzed Branch-Selective Allylic C–H Amination Enabled by Nucleophile Coordination

Regiochemical control is a central subject in the field of synthetic chemistry. Here we unveil an innovative approach for the branch-selective allylic C-H amination of α-alkenes with amine nucleophiles facilitated by phosphoramidite-palladium catalysis. A diverse array of α-alkenes has been effectively utilized to produce a variety of structurally distinct allylamines with moderate to excellent regioselectivity. Furthermore, the asymmetric version of this reaction is feasible through the use of chiral phosphoramidite ligands, albeit with currently modest enantioselectivity.

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Publication Details

Journal
Organic Letters
Published
2024-09-27
DOI
https://doi.org/10.1021/acs.orglett.4c02935
Citations
8
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
2.00

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article

Palladium-Catalyzed Branch-Selective Allylic C–H Amination Enabled by Nucleophile Coordination

Zhong‐Sheng Nong, Qi‐Lin Zhou, Liu‐Zhu Gong, Pu‐Sheng Wang
8 citations
Organic Letters
Catalytic C–H Functionalization Methods
2.00
article

Palladium-Catalyzed Branch-Selective Allylic C–H Amination Enabled by Nucleophile Coordination

Zhong‐Sheng Nong, Qi‐Lin Zhou, Liu‐Zhu Gong, Pu‐Sheng Wang
article en
8 citations

Abstract

Regiochemical control is a central subject in the field of synthetic chemistry. Here we unveil an innovative approach for the branch-selective allylic C-H amination of α-alkenes with amine nucleophiles facilitated by phosphoramidite-palladium catalysis. A diverse array of α-alkenes has been effectively utilized to produce a variety of structurally distinct allylamines with moderate to excellent regioselectivity. Furthermore, the asymmetric version of this reaction is feasible through the use of chiral phosphoramidite ligands, albeit with currently modest enantioselectivity.

Organic LettersVol. 26(40)
University of Science and Technology of China (CN), Nankai University (CN), Hefei National Center for Physical Sciences at Nanoscale (CN)
National Natural Science Foundation of China, Youth Innovation Promotion Association of the Chinese Academy of Sciences, University of Science and Technology of China, National Key Research and Development Program of China
Openalex Percentile: Top 14%
Catalytic C–H Functionalization Methods
2.00
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