A Unified Photocatalytic Strategy for Fluoroalkylated and Cyanated α-Tertiary Amino/Glycolic Acids via a Radical-Polar Cascade
A redox-neutral, metal-free, visible-light-driven strategy is developed for constructing fluoroalkylated and cyanated α-tertiary amino acids (ATAAs) via a radical migration-mediated radical-polar cascade. This mild protocol generates multifunctional α-carbonyl carbocations, which are trapped by nitriles to afford diverse ATAAs with a broad scope. The synthetic utility is demonstrated through the late-stage modification of bioactive molecules. Remarkably, trapping the carbocations with H<sub>2</sub>O provides fluoroalkylated and cyanated α-tertiary glycolic acids (ATGAs) in good yields, thus offering a powerful tool for privileged pharmaceutical scaffold development.
Authors
- Man‐Yi Han (ORCID: https://orcid.org/0000-0001-7448-8924)
- Chi Zhang (ORCID: https://orcid.org/0000-0002-1827-8137)
- Rui Zhu (ORCID: https://orcid.org/0000-0001-7820-129X)
- Lei Jin (ORCID: https://orcid.org/0000-0002-7710-353X)
- Ya-Zhen Zeng
- Peng Wang (ORCID: https://orcid.org/0009-0002-4416-6339)
Institutions
- Ministry of Education of the People's Republic of China (CN)
- Huaibei Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-22
- DOI
- https://doi.org/10.1021/acs.orglett.5c02796
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Huaibei Normal University