Transient Directing Group Enabled Nickel-Catalyzed Satoh–Miura Annulation of Free Benzylamines with Alkynes

We report a nickel-catalyzed Satoh-Miura annulation of free benzylamines with alkynes, enabled by a transient directing group (TDG) strategy. The integration of the TDG approach with earth-abundant nickel catalysis provides a straightforward and efficient route for the synthesis of substituted 1-naphthylmethylamines, which exhibits excellent functional group tolerance. Compared with conventional directing group (DG)-directed precious-metal-catalyzed systems for polycyclic aromatic hydrocarbon (PAH) synthesis, this protocol demonstrates advantages in atom- and step-economy, cost effectiveness, and sustainability.

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Publication Details

Journal
Organic Letters
Published
2025-12-08
DOI
https://doi.org/10.1021/acs.orglett.5c03914
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Transient Directing Group Enabled Nickel-Catalyzed Satoh–Miura Annulation of Free Benzylamines with Alkynes

Chen Ma, Weiwei Li, Shiming Fan, Zhi‐Gang She et al.
Organic Letters
Catalytic C–H Functionalization Methods
article

Transient Directing Group Enabled Nickel-Catalyzed Satoh–Miura Annulation of Free Benzylamines with Alkynes

Chen Ma, Weiwei Li, Shiming Fan, Zhi‐Gang She, Jinlong Liu, Yi Ren, Ying Kang, Xue Meng, Xinghao Cai, Shouxin Liu
article en

Abstract

We report a nickel-catalyzed Satoh-Miura annulation of free benzylamines with alkynes, enabled by a transient directing group (TDG) strategy. The integration of the TDG approach with earth-abundant nickel catalysis provides a straightforward and efficient route for the synthesis of substituted 1-naphthylmethylamines, which exhibits excellent functional group tolerance. Compared with conventional directing group (DG)-directed precious-metal-catalyzed systems for polycyclic aromatic hydrocarbon (PAH) synthesis, this protocol demonstrates advantages in atom- and step-economy, cost effectiveness, and sustainability.

Organic LettersVol. 27(50)
Hebei University of Science and Technology (CN), Hebei Chemical and Pharmaceutical College (CN)
Openalex Percentile: Top 71%
Catalytic C–H Functionalization Methods
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