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Published on: July 28, 2022
Selective hydroboration of equilibrating allylic azides.
Ruzhang Liu1, Yuanyuan Zhang1, Jun Xu1
1College of Chemistry & Chemical Engineering, Yangzhou University, 180 Siwangting Rd, Yangzhou 225002, China. liurzh@yzu.edu.cn.
Iridium(I) catalysis enables the hydroboration of allylic azides to exclusively yield anti-Markovnikov alk-1-ene products. This reaction demonstrates excellent functional group tolerance and good yields, offering a valuable synthetic route.
Area of Science:
- Organometallic chemistry
- Catalysis
- Synthetic organic chemistry
Background:
- Allylic azides are versatile synthetic intermediates.
- Hydroboration reactions are crucial for C-B bond formation.
- Controlling regioselectivity in hydroboration of dynamic substrates is challenging.
Purpose of the Study:
- To investigate the iridium(I)-catalyzed hydroboration of equilibrating allylic azides.
- To determine the regioselectivity and functional group tolerance of the reaction.
- To develop a novel synthetic method for accessing specific alkene isomers.
Main Methods:
- Utilizing an iridium(I) catalyst for the hydroboration reaction.
- Employing equilibrating allylic azides as substrates.
- Analyzing reaction products using standard spectroscopic techniques (e.g., NMR).
Main Results:
- The reaction exclusively afforded the anti-Markovnikov product, alk-1-ene isomers.
- Good yields were obtained for the desired products.
- The catalytic system exhibited broad functional group tolerance.
Conclusions:
- Iridium(I)-catalyzed hydroboration provides a highly regioselective route to anti-Markovnikov alkenes from allylic azides.
- The method is efficient and compatible with various functional groups.
- This offers a valuable new strategy in synthetic organic chemistry.
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