Photoinduced Concerted Fragmentation of Alkyl <i>N</i>-Phthalimidoyl Oxalates: Mechanisms and Applications
In this work, we used experiments and density functional theory calculations to investigate the mechanism and driving forces of the reductive fragmentation of NHPI esters. Mechanistic studies suggest that the fragmentation behavior of the NHPI ester is influenced not only by the electronic nature of the substituent group but also by the stability of the radical intermediate. To further investigate this transformation, we next examined the aminoalkoxycarbonylation of alkenes using alkyl <i>N</i>-phthalimidoyl oxalates. With this approach, a variety of β-amino acid derivatives with diverse structures can be obtained in moderate to high yields.
Authors
- Jiapian Huang (ORCID: https://orcid.org/0000-0002-7463-1572)
- Jie Wu (ORCID: https://orcid.org/0000-0002-0967-6360)
- Xiaoyu Zhou (ORCID: https://orcid.org/0000-0002-3552-3595)
- Tong Wang (ORCID: https://orcid.org/0000-0002-4930-6284)
- Jianqiang Chen (ORCID: https://orcid.org/0000-0001-6911-1858)
- Yuanxiang Feng (ORCID: https://orcid.org/0000-0002-1507-6310)
- J. Yao
- Min Yang (ORCID: https://orcid.org/0000-0001-8338-9725)
Institutions
- Jiangxi University of Traditional Chinese Medicine (CN)
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Gannan Medical University (CN)
- State Key Laboratory of Organometallic Chemistry
- Henan Normal University (CN)
- Taizhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-12-26
- DOI
- https://doi.org/10.1021/acs.orglett.4c04465
- Citations
- 8
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 2.00
Funders
- National Natural Science Foundation of China
- Zhejiang Provincial Ten Thousand Plan for Young Top Talents
- Natural Science Foundation of Zhejiang Province