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Radical trifunctionalization of hexenenitrile via remote cyano migration
Chenyang Chang1, Huihui Zhang1, Xinxin Wu1
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, China. chzhu@suda.edu.cn.
Chemical Communications (Cambridge, England)
|December 23, 2021
Summary
This study introduces a new method for trifunctionalization of hexenenitriles using remote cyano migration and azido radical capture. This approach creates complex molecules with multiple functional groups under mild conditions.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Remote functional group migration is a key strategy in organic synthesis.
- Developing efficient methods for trifunctionalization of alkenes remains a challenge.
Purpose of the Study:
- To disclose a novel radical-mediated trifunctionalization of hexenenitriles.
- To expand the utility of remote functional group migration in complex molecule synthesis.
Main Methods:
- Utilizing functionalized hexenenitriles as substrates.
- Employing a radical-mediated pathway involving remote cyano migration.
- Capturing the in situ formed radical intermediate with an azido radical.
Main Results:
- Successful trifunctionalization of hexenenitriles was achieved.
- The reaction proceeds under mild conditions with broad functional group compatibility.
- Valuable products bearing multiple useful groups were synthesized.
Conclusions:
- The developed protocol offers an efficient route to complex functionalized hexenenitriles.
- This method significantly extends the scope and applicability of remote functional group migration strategies.
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