Alharthi, Asma A;
Kariuki, Benson M;
Morrill, Louis C;
Browne, Duncan L;
(2026)
Mechanochemical one-pot Barbier/Simmons-Smith reaction via sequential zinc activation.
Chemical Communications
, 62
(6)
pp. 1864-1868.
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.
| Type: | Article |
|---|---|
| Title: | Mechanochemical one-pot Barbier/Simmons-Smith reaction via sequential zinc activation |
| Location: | England |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1039/d5cc05732a |
| Publisher version: | https://doi.org/10.1039/d5cc05732a |
| Language: | English |
| Additional information: | This work is licensed under a Creative Commons License. The images or other third-party material in this article are included in the Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit https://creativecommons.org/licenses/by-nc/4.0/deed.en |
| Keywords: | Science & Technology, Physical Sciences, Chemistry, Multidisciplinary, Chemistry, BARBIER-TYPE ALLYLATION, GRIGNARD-REAGENTS, ALDEHYDES, METAL |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10221362 |
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