Direct oxidative conversion of methylarenes into aromatic nitriles
Daisuke Tsuchiya1, Yuhsuke Kawagoe, Katsuhiko Moriyama
1Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.
Organic Letters
|August 2, 2013
Summary
This study presents a new, practical method for synthesizing aromatic nitriles from methylarenes using readily available reagents. The transition-metal-free process offers good yields in a convenient one-pot procedure.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Aromatic nitriles are important building blocks in organic synthesis.
- Existing methods for synthesizing aromatic nitriles can be costly or inefficient.
Purpose of the Study:
- To develop a novel, transition-metal-free method for preparing aromatic nitriles from methylarenes.
- To establish a practical and efficient one-pot synthesis of aromatic nitriles.
Main Methods:
- Utilizing N-bromosuccinimide (NBS) or 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) with a radical initiator (AIBN or BPO).
- Subsequent reaction with molecular iodine in aqueous ammonia in a one-pot sequence.
- Employing methylarenes as starting materials.
Main Results:
- Successful conversion of various methylarenes into corresponding aromatic nitriles.
- Achieved good to moderate yields for the synthesized aromatic nitriles.
- Demonstrated the efficiency of the one-pot procedure.
Conclusions:
- The developed method is a useful and practical transition-metal-free route for aromatic nitrile preparation.
- This approach provides an accessible pathway for synthesizing aromatic nitriles from methylarenes.
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