Synthesis of α‑Haloboronates by the Halogenation of gem-Diborylalkanes via Tetracoordinate Boron Species

α-Haloboronates have a wide range of applications in organic chemistry as synthetic synthons; however, traditional synthetic methods of α-haloboronates are harsh and complicated. Herein, we used n BuLi as the nucleophilic reagent to attack the boron atom in gem-diborylalkanes to form tetracoordinate...

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Bibliographic Details
Published in:Organic letters 2023-04, Vol.25 (16), p.2928-2933
Main Authors: Liao, Shangteng, Liang, Jinchao, Li, Chaokun, Chen, Nan, Yang, Kai, Chen, Jinglong, Song, Qiuling
Format: Article
Language:English
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Summary:α-Haloboronates have a wide range of applications in organic chemistry as synthetic synthons; however, traditional synthetic methods of α-haloboronates are harsh and complicated. Herein, we used n BuLi as the nucleophilic reagent to attack the boron atom in gem-diborylalkanes to form tetracoordinate boron species and successfully achieved α-chloroboronates and α-bromoboronates with readily accessible electrophilic halogen reagents (NCS and NBS). The reaction is transition-metal-free and features a broad substrate scope and diversified valuable products.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c00982