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Sequential α/β-C-H Functionalization of Monosubstituted Aliphatic Alkenes
Yini Wang1, Bingbing Xie1, Chengxing Peng1
1Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Zhejiang Key Laboratory of Organosilicon Material Technology, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121, Zhejiang, China.
This study introduces a novel method for sequential C-H functionalization of monosubstituted aliphatic alkenes. The new protocol enables efficient alkenylation, allylation, and alkynylation with high selectivity.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Monosubstituted alkenes are crucial building blocks in organic synthesis.
- Chelation-assisted alkenyl C-H functionalization has advanced, but challenges remain for monosubstituted aliphatic alkenes due to reactivity and selectivity.
Purpose of the Study:
- To develop the first sequential α/β-C-H functionalization protocol for monosubstituted aliphatic alkenes.
- To address the limitations in reactivity and selectivity for these challenging substrates.
Main Methods:
- Utilized bishomoallyl amines as starting materials.
- Developed a sequential C-H functionalization strategy targeting both alpha and beta positions.
Main Results:
- Achieved successful C-H alkenylation, allylation, and alkynylation.
- Demonstrated wide functional group tolerance.
- Obtained products with excellent regio- and stereoselectivity.
Conclusions:
- The developed protocol represents a significant advancement in the C-H functionalization of monosubstituted aliphatic alkenes.
- This method offers a versatile and efficient route to complex organic molecules.
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