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RHAT-Enabled Deoxyfunctionalization of Cyclic Acetals Derived from Vicinal Diols.
Zheng Wang1, Huiying Liu1, Tiantian Liu1
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, China.
This study presents a new radical deoxygenative strategy to functionalize cyclic acetals from diols. The method efficiently synthesizes deconjugated alkenes using visible-light-driven conditions.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Selective activation of strong carbon-oxygen (C-O) bonds in diols is challenging due to high bond energies.
- Existing methods for diol functionalization often lack regioselectivity or require harsh conditions.
Purpose of the Study:
- To develop a regioselective radical deoxygenative strategy for functionalizing cyclic acetals derived from vicinal diols.
- To synthesize deconjugated alkenes under mild, visible-light-driven conditions.
Main Methods:
- Utilized a visible-light-driven radical deoxygenative approach.
- Employed cyclic acetals derived from vicinal diols and various alkynes as substrates.
- Conducted mechanistic studies including radical trapping, isotopic labeling, and density functional theory (DFT) calculations.
Main Results:
- Achieved regioselective synthesis of deconjugated alkenes from six-membered and larger cyclic acetals.
- Demonstrated broad substrate scope for both cyclic acetals and alkynes.
- Obtained moderate to excellent yields and high regioselectivity in product formation.
Conclusions:
- Established a novel platform for site-selective functionalization of vicinal diols.
- Highlighted the potential of regioselective hydrogen atom transfer (RHAT)-enabled strategies for C-O bond activation.
- The proposed mechanism involves a sequential RHAT/radical addition/RHAT/C-O cleavage pathway.
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