Metal‐Free Cleavage of C(sp <sup>3</sup> )─C(sp <sup>3</sup> ) Bonds for α‐Acyloxy Ethers With Iodine (III) as Co‐Oxidant and Coupling Reagent
ABSTRACT A metal‐free selective cleavage of saturated C(sp 3 )─C(sp 3 ) bonds in glycol ethers mediated by free radicals is reported. This process utilizes O 2 as the terminal stoichiometric oxidant, hypervalent iodine(III) reagents as the co‐oxidants, and coupling reagents. This reaction avoids the use of metal catalysts and azides (for preparing BIN 3 ), and the iodine reagent is suitable for long‐term storage. Under the synergistic action of hypervalent iodine(III) reagents and O 2 , various types of cyclic and linear alkyl ethers can be efficiently transformed into benzoylated acetals and aldehydes. The control experiments and mechanistic studies offer a plausible mechanism explanation for this process of cleavage of C(sp 3 )─C(sp 3 ) bonds.
Authors
- Lei Guo (ORCID: https://orcid.org/0000-0003-2055-7618)
- Xi Zhang (ORCID: https://orcid.org/0000-0002-4638-3997)
- Jiaping Zhang (ORCID: https://orcid.org/0000-0002-0595-7202)
- Fufang Wu
- Xiaobao Shen
- Chunmei Tang
- Hongbin Zhai
- Shuxin Wang
Institutions
- Fuyang Normal University (CN)
- Shenzhen University (CN)
- Peking University (CN)
- Anhui Science and Technology University (CN)
Publication Details
- Journal
- Asian Journal of Organic Chemistry
- Published
- 2026-03-01
- DOI
- https://doi.org/10.1002/ajoc.70365
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00