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.
Authors
- Huatao Wu
- Xin‐Rong Yao
- Jiuxi Chen (ORCID: https://orcid.org/0000-0001-6666-9813)
- Mao‐Lin Hu (ORCID: https://orcid.org/0000-0003-4130-9859)
- Min Liu (ORCID: https://orcid.org/0000-0002-9007-4817)
- Ge Zeng
- Renhao Li (ORCID: https://orcid.org/0000-0003-2451-2142)
- Xiaoxia Ye
Institutions
- 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)
Publication Details
- 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
- 0.00
Funders
- National Natural Science Foundation of China
- Wenzhou Municipal Science and Technology Bureau
- Natural Science Foundation of Zhejiang Province