Visible-Light-Induced Divergent C–H Esterification/Alkylation of Quinoxalin-2(1<i>H</i>)-ones with Aldehydes under Mild Conditions
Herein, we introduce an efficient and straightforward strategy for the selective C-H esterification and alkylation of quinoxalin-2(1<i>H</i>)-ones with aldehydes. A key feature of our study is the ability to perform both C-H esterification and alkylation using different types of aldehydes. The reaction system is highly compatible with a range of quinoxalin-2(1<i>H</i>)-ones and aldehydes, yielding C3-esterified and C3-alkylated products in moderate-to-good yields. The applicability of this approach is further enhanced by its scalability through continuous-flow synthesis, late-stage modification of significant molecules, and product derivatization. Our mechanistic investigations reveal a radical relay mechanism, triggered by a hydrogen atom transfer process.
Authors
- Yan Du (ORCID: https://orcid.org/0000-0003-3197-7204)
- G.D. Wang
- Hong Yu (ORCID: https://orcid.org/0000-0002-6819-6607)
- Jiabin Shen (ORCID: https://orcid.org/0009-0009-0908-8946)
- Chen An (ORCID: https://orcid.org/0000-0002-7787-1483)
- Pengfei Zhang (ORCID: https://orcid.org/0000-0001-9859-0237)
- Jun Xu (ORCID: https://orcid.org/0000-0003-0519-1056)
Institutions
- Hangzhou Normal University (CN)
- Kementerian Pendidikan Malaysia (MY)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-03-05
- DOI
- https://doi.org/10.1021/acs.orglett.5c00631
- Citations
- 25
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 23.40
Funders
- National Natural Science Foundation of China
- Science and Technology Department of Zhejiang Province