Pd-Catalyzed Tandem Reaction of [1,1′-Biaryl]-2,2′-dimethylnitriles with Arylboronic Acids: Synthesis of 7-Aryl-2<i>H</i>-azepin-2-ones

The palladium-catalyzed addition-cyclization cascade of [1,1'-biaryl]-2,2'-dimethylnitriles with arylboronic acids was developed, providing an efficient one-pot strategy for constructing 7-aryl-2<i>H</i>-azepin-2-one scaffolds. The protocol demonstrates excellent chemoselectivity, enabling the synthesis of benzo[<i>c</i>]pyrido[2,3-<i>e</i>]azepin and benzo[<i>c</i>]thieno[3,2-<i>e</i>]azepin scaffolds through the selective aryl addition of arylboronic acids to the electron-rich aryl nitrile moiety. The method demonstrates the use of easy availability starting materials, achieving high efficiency, broad applicability across diverse substrates, and excellent functional group compatibility.

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Journal
The Journal of Organic Chemistry
Published
2025-06-09
DOI
https://doi.org/10.1021/acs.joc.5c01039
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
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article

Pd-Catalyzed Tandem Reaction of [1,1′-Biaryl]-2,2′-dimethylnitriles with Arylboronic Acids: Synthesis of 7-Aryl-2H-azepin-2-ones

Huatao Wu, Xin‐Rong Yao, Jiuxi Chen, Mao‐Lin Hu et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Pd-Catalyzed Tandem Reaction of [1,1′-Biaryl]-2,2′-dimethylnitriles with Arylboronic Acids: Synthesis of 7-Aryl-2H-azepin-2-ones

Huatao Wu, Xin‐Rong Yao, Jiuxi Chen, Mao‐Lin Hu, Min Liu, Ge Zeng, Renhao Li, Xiaoxia Ye
article en

Abstract

The palladium-catalyzed addition-cyclization cascade of [1,1'-biaryl]-2,2'-dimethylnitriles with arylboronic acids was developed, providing an efficient one-pot strategy for constructing 7-aryl-2<i>H</i>-azepin-2-one scaffolds. The protocol demonstrates excellent chemoselectivity, enabling the synthesis of benzo[<i>c</i>]pyrido[2,3-<i>e</i>]azepin and benzo[<i>c</i>]thieno[3,2-<i>e</i>]azepin scaffolds through the selective aryl addition of arylboronic acids to the electron-rich aryl nitrile moiety. The method demonstrates the use of easy availability starting materials, achieving high efficiency, broad applicability across diverse substrates, and excellent functional group compatibility.

The Journal of Organic ChemistryVol. 90(24)
Sinopec (China) (CN), Wenzhou University (CN), Wenzhou Medical University (CN), Institute of Macromolecular Chemistry (UA), Beijing Chemical Industry Research Institute (China) (CN), Division of Materials Science and Engineering (AU)
National Natural Science Foundation of China, Wenzhou Municipal Science and Technology Bureau, Natural Science Foundation of Zhejiang Province
Openalex Percentile: Top 90%
Catalytic C–H Functionalization Methods
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