Published September 6, 2019
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Journal Article
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Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism
Abstract
We describe an operationally simple transition-metal-free borylation of alkyl iodides. This method uses commercially available diboron reagents as the boron source and exhibits excellent functional group compatibility. Furthermore, a diverse range of primary and secondary alkyl iodides could be effectively transformed to the corresponding alkylboronates in excellent yield. Mechanistic investigations suggest that this borylation reaction proceeds through a single-electron transfer mechanism featuring the generation of an alkyl radical intermediate.
Additional Information
© 2019 American Chemical Society. Received: June 5, 2019; Published: June 25, 2019. We thank Prof. Lei Jiao at Tsinghua University for DFT calculation consultation. The project was supported by the Natural Science Foundation of China (Grant 21772003). We also thank Peking University for a start-up fund. This work was also partially funded by the BHP-PKU CCUS project supported by BHP Billiton. The authors declare no competing financial interest.Attached Files
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Additional details
- Eprint ID
- 96711
- DOI
- 10.1021/acs.orglett.9b01951
- Resolver ID
- CaltechAUTHORS:20190625-161756099
- 21772003
- National Natural Science Foundation of China
- Peking University
- BHP Billiton
- Created
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2019-06-26Created from EPrint's datestamp field
- Updated
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2021-11-16Created from EPrint's last_modified field