Mechanochemical Synthesis of α‐halo Alkylboronic Esters

α‐halo alkylboronic esters, acting as ambiphilic synthons, play a pivotal role as versatile intermediates in fields like pharmaceutical science and organic chemistry. The sequential transformation of carbon–boron and carbon–halogen bonds into a broad range of carbon–X bonds allows for programmable b...

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Bibliographic Details
Published in:	Advanced science Vol. 11; no. 33; pp. e2404071 - n/a
Main Authors:	Zhao, Yunyi, Yang, Zekun, Wang, Xin, Kang, Qinchun, Wang, Bobo, Wu, Tianle, Lei, Hao, Ma, Peile, Su, Wenqiang, Wang, Siyuan, Wu, Zhiqiang, Huang, Xinsong, Fan, Chunying, Wei, Xiaofeng
Format:	Journal Article
Language:	English
Published:	Germany John Wiley & Sons, Inc 01-09-2024 John Wiley and Sons Inc Wiley
Subjects:	Chemistry external catalyst‐free halogenation mechanochemical Potassium radical relayed Solvents α‐halo alkylboronic esters radical relayed external catalyst‐free halogenation mechanochemical α‐halo alkylboronic esters
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Summary:	α‐halo alkylboronic esters, acting as ambiphilic synthons, play a pivotal role as versatile intermediates in fields like pharmaceutical science and organic chemistry. The sequential transformation of carbon–boron and carbon–halogen bonds into a broad range of carbon–X bonds allows for programmable bond formation, facilitating the incorporation of multiple substituents at a single position and streamlining the synthesis of complex molecules. Nevertheless, the synthetic potential of these compounds is constrained by limited reaction patterns. Additionally, the conventional methods often necessitate the use of bulk toxic solvents, exhibit sensitivity to air/moisture, rely on expensive metal catalysts, and involve extended reaction times. In this report, a ball milling technique is introduced that overcomes these limitations, enabling the external catalyst‐free multicomponent coupling of aryl diazonium salts, alkenes, and simple metal halides. This approach offers a general and straightforward method for obtaining a diverse array of α‐halo alkylboronic esters, thereby paving the way for the extensive utilization of these synthons in the synthesis of fine chemicals. An external catalyst‐free and solvent‐less mechanochemical protocol is developed for the direct synthesis of α‐halo alkylboronic esters. This reaction features mild conditions, including short reaction times and the absence of both solvents and external catalysts. The simplicity of the procedure makes this methodology both sustainable and cost‐effective.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	2198-3844 2198-3844
DOI:	10.1002/advs.202404071