Transition-Metal-Free Borylation of Alkyl Iodides via a Radical Mechanism

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 effe...

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Bibliographic Details
Published in:Organic letters 2019-09, Vol.21 (17), p.6597-6602
Main Authors: Liu, Qianyi, Hong, Junting, Sun, Beiqi, Bai, Guangcan, Li, Feng, Liu, Guoquan, Yang, Yang, Mo, Fanyang
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01951