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Synthesis
DOI: 10.1055/a-2801-5094
Paper
Published as part of 22nd International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-22)

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

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

  • Koji Kubota

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

  • Hajime Ito 

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

The authors gratefully acknowledge the financial support from JSPS KAKENHI grants 24H00453 (to K.K.), 24H01050 (to K.K.), 24H01832 (to K.K.), 22H00318 (to H.I.), and 22K18333 (to H.I.), as well as from JST via a CREST grant JPMJCR19R1 (to H.I.) and FOREST grant JPMJFR201I (to K.K.). The authors are also grateful to the Institute for Chemical Reaction Design and Discovery (ICReDD) established by the World Premier International Research Initiative (WPI), MEXT, Japan.
Supported by: JSPS KAKENHI 22H00318,22K18333,24H00453,24H01050,24H01832
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Graphical Abstract

Abstract

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.

Keywords

Debenzylation - Mechanochemistry - Ball milling - Birch reduction - Sodium


Publication History

Received: 08 December 2025

Accepted after revision: 29 January 2026

Accepted Manuscript online:
29 January 2026

Article published online:
26 February 2026

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