Mechanochemical one-pot Barbier/Simmons–Smith reaction via sequential zinc activation

Alharthi, Asma A., Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897, Morrill, Louis C. ORCID: https://orcid.org/0000-0002-6453-7531 and Browne, Duncan L. ORCID: https://orcid.org/0000-0002-8604-229X 2025. Mechanochemical one-pot Barbier/Simmons–Smith reaction via sequential zinc activation. Chemical Communications 10.1039/d5cc05732a

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Abstract

We report a mechanochemical one-pot Barbier/Simmons–Smith reaction enabled by ball-milling-mediated activation of zinc(0). This operationally simple method generates organozinc intermediates in situ and uses them sequentially in allylation and cyclopropanation without intermediate work-up. The protocol tolerates a broad range of ketones, exhibits selectivity over other carbonyl groups, and is compatible with various physical forms of zinc metal. In selected cases, the reaction proceeds with markedly enhanced diastereoselectivity under minimal-solvent milling conditions and was demonstrated on a gram scale using standard ball-milling equipment. Comparative studies show advantages over conventional solution and neat conditions, highlighting how mechanochemistry can uniquely enable tandem organometallic processes as for C–C bond construction.

Item Type:	Article
Date Type:	Published Online
Status:	In Press
Schools:	Schools > Chemistry Research Institutes & Centres > Cardiff Catalysis Institute (CCI)
Additional Information:	License information from Publisher: LICENSE 1: URL: https://creativecommons.org/licenses/by-nc/3.0/, Start Date: 2025-12-23
Publisher:	Royal Society of Chemistry
ISSN:	1359-7345
Date of First Compliant Deposit:	6 January 2026
Date of Acceptance:	11 December 2025
Last Modified:	06 Jan 2026 12:01
URI:	https://orca.cardiff.ac.uk/id/eprint/183587

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