Cyclic Iodonium Ylide Unlocked Pd-Catalyzed α-Acyloxylation of Cyclic 1,3-Dicarbonyls with Carboxylic Acids
To date, a general approach for the direct α-acyloxylation of cyclic 1,3-dicarbonyls remains challenging. Herein, we report a Pd-catalyzed α-acyloxylation of cyclic 1,3-dicarbonyl-derived hypervalent iodine compounds with highly abundant carboxylic acids. Our approach utilizes a commercially available Pd(OAc)<sub>2</sub> catalyst, which exhibits mild reaction conditions, scalability, operational simplicity, and robustness against moisture and air. Importantly, our approach eliminates the need for excess carboxylic acids (only 1 equiv) and the use of explosive peroxides and is compatible with diverse complex substrates (e.g., glycyrrhetinic acid and celastrol). The power of this method is further demonstrated through significantly simplifying a previous synthesis.
Authors
- Bin Yang (ORCID: https://orcid.org/0000-0001-7948-3823)
- H. -L. Cui
- Hui Xiong (ORCID: https://orcid.org/0000-0003-4138-2992)
- Huanping Xie (ORCID: https://orcid.org/0000-0003-3289-2384)
- Shaoyu Mai (ORCID: https://orcid.org/0000-0002-9318-7606)
- Huaming Tao (ORCID: https://orcid.org/0000-0002-4799-1345)
- Zhenwei Zhang (ORCID: https://orcid.org/0000-0003-1521-5728)
- Borong Su
Institutions
- Chinese Academy of Sciences (CN)
- Institute of Oceanology (CN)
- South China Sea Institute Of Oceanology (CN)
- Nanyang Normal University (CN)
- Southern Medical University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-12-10
- DOI
- https://doi.org/10.1021/acs.joc.4c02492
- Citations
- 6
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.50
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Guangdong Province
- Special Project for Research and Development in Key areas of Guangdong Province