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Synthesis
DOI: 10.1055/a-2801-5094
Paper

Sodium-lump-mediated mechanochemical deprotection of benzyl-derived groups

Authors

  • Keisuke Kondo

    1   Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Japan (Ringgold ID: RIN12810)

  • Naoki Shizukuishi

    2   Division of Applied Chemistry, Hokkaido University, Sapporo, Japan (Ringgold ID: RIN12810)

  • Koji Kubota

    3   Faculty of Engineering, Hokkaido University, Sapporo, Japan (Ringgold ID: RIN12810)
    4   Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Japan (Ringgold ID: RIN12810)

  • Hajime Ito 

    2   Division of Applied Chemistry, Hokkaido University, Sapporo, Japan (Ringgold ID: RIN12810)
    4   Institute for Chemical Reaction Design and Discovery (WPI-ICReDD), Hokkaido University, Sapporo, Japan (Ringgold ID: RIN12810)

Supported by: Japan Science and Technology Corporation JPMJCR19R1,JPMJFR201I
Supported by: JSPS KAKENHI 22H00318,22K18333,24H00453,24H01050,24H01832
Further Information
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This study demonstrates the facile removal of benzyl-derived protecting groups via ammonia-free, mechanochemically driven Birch reduction using inexpensive and easy-to-handle sodium lumps. Various benzyl-protected alcohols and amines were efficiently deprotected within 30 min. Notably, all synthetic operations can be performed without inert gases or bulk solvents.



Publication History

Received: 08 December 2025

Accepted after revision: 29 January 2026

Accepted Manuscript online:
29 January 2026

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