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A silylene-stabilized distannavinylidene with a highly labile substituent

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Abstract

Vinylidene and its heavier analogues are fundamentally important in synthetic chemistry, but their stabilization and structural characterization remains extremely challenging. Herein we describe that the reduction of an NHSi-stabilized stannyl-stannylene (2) with one molar equivalent of [(MesNacnac)Mg]2 affords an NHSi-stabilized distannavinylidene (3). Single-crystal X-ray crystallography and density functional theory (DFT) calculations show that compound 3 features a pronounced Sn=Sn double bond and one lone pair of electrons at the two-coordinate Sn atom. Most strikingly, 3 undergoes an interconversion with distannyne (4) upon the addition and removal of one molar equivalent of N-heterocyclic carbene. Compound 3 readily reacts with Ph2C=C=O, AdC≡P and (AlCp*)4 to give the structurally interesting stannacycles (5, 6) and an aluminyl distannyne (7), demonstrating its unique reactivity derived from the high substituent lability.

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Acknowledgements This work was supported by the National Natural Science Foundation of China (22071124, 22371130, 22221002), the Frontiers Science Center for New Organic Matter at Nankai University (C029215001), the Fundamental Research Funds for the Central Universities (63206007), the Nankai University and Young Elite Scientists Sponsorship Program by Tianjin.

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin, 300071, China

    Zihao Qiao, Ming Chen & Zhenbo Mo

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  1. Zihao Qiao
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  2. Ming Chen
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  3. Zhenbo Mo
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Correspondence to Zhenbo Mo.

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Conflict of interest The authors declare no conflict of interest.

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Supporting information The supporting information is available online at https://www.chem.scichina.com and https://www.link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Qiao, Z., Chen, M. & Mo, Z. A silylene-stabilized distannavinylidene with a highly labile substituent. Sci. China Chem. 66, 3555–3561 (2023). https://doi.org/10.1007/s11426-023-1855-y

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  • DOI: https://doi.org/10.1007/s11426-023-1855-y

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