Mechanochemical synthesis of organoselenium compounds

Shanshan Chen, Chunying Fan, Zijian Xu, Mengyao Pei, Jiemin Wang, Jiye Zhang, Yilei Zhang, Jiyu Li, Junliang Lu, Cheng Peng () and Xiaofeng Wei ()
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Shanshan Chen: Xi’an Jiaotong University
Chunying Fan: Xi’an Jiaotong University
Zijian Xu: Chinese Academy of Sciences
Mengyao Pei: Xi’an Jiaotong University
Jiemin Wang: Xi’an Jiaotong University
Jiye Zhang: Xi’an Jiaotong University
Yilei Zhang: Xi’an Jiaotong University Health Science Center
Jiyu Li: Xi’an Aisiyi Health Industry Co., Ltd
Junliang Lu: Xi’an Aisiyi Health Industry Co., Ltd
Cheng Peng: Xi’an Jiaotong University
Xiaofeng Wei: Xi’an Jiaotong University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract We disclose herein a strategy for the rapid synthesis of versatile organoselenium compounds under mild conditions. In this work, magnesium-based selenium nucleophiles are formed in situ from easily available organic halides, magnesium metal, and elemental selenium via mechanical stimulation. This process occurs under liquid-assisted grinding (LAG) conditions, requires no complicated pre-activation procedures, and operates broadly across a diverse range of aryl, heteroaryl, and alkyl substrates. In this work, symmetrical diselenides are efficiently obtained after work-up in the air, while one-pot nucleophilic addition reactions with various electrophiles allow the comprehensive synthesis of unsymmetrical monoselenides with high functional group tolerance. Notably, the method is applied to regioselective selenylation reactions of diiodoarenes and polyaromatic aryl halides that are difficult to operate via solution approaches. Besides selenium, elemental sulfur and tellurium are also competent in this process, which showcases the potential of the methodology for the facile synthesis of organochalcogen compounds.

Date: 2024
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DOI: 10.1038/s41467-024-44891-2

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