Photoredox-Mediated Alkylation of Oxime Chlorides for the Stereoselective Synthesis of Ketoximes
Oximes are valuable motifs in bioactive molecules and serve as versatile synthetic intermediates. However, the stereoselective synthesis of aryl alkyl ketoximes remains challenging due to the formation of (<i>E</i>/<i>Z</i>)-isomer mixtures from traditional methods. We report a modular, efficient photochemical strategy that couples alkyl radicals with oxime chlorides to yield ketoximes stereoselectively. Mechanistic studies reveal a radical coupling and photoisomerization pathway via visible-light-driven energy transfer catalysis.
Authors
- Yu‐hong Lam (ORCID: https://orcid.org/0000-0002-4946-1487)
- Le Dung Pham (ORCID: https://orcid.org/0000-0002-5028-2785)
- Ruoyu Zoe Qian (ORCID: https://orcid.org/0000-0002-5561-5067)
- Shorouk O. Badir (ORCID: https://orcid.org/0000-0003-4634-0644)
- Sabrina N. Carneiro (ORCID: https://orcid.org/0009-0008-0771-482X)
- Zhixun Wang (ORCID: https://orcid.org/0000-0001-5688-5002)
Institutions
- Merck & Co., Inc., Rahway, NJ, USA (United States) (US)
- Institute of Computational Modeling (RU)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-10-23
- DOI
- https://doi.org/10.1021/acs.orglett.5c03845
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00