Synlett 2025; 36(04): 389-391
DOI: 10.1055/a-2347-1143
letter

Earth-Abundant Metal-Catalyzed Cross-Coupling Reactions of 1-Bromocyclobut-1-enes with Grignard Reagents

Tomohiro Yasukawa
a   ESPCI Paris – PSL, CNRS, 10 Rue Vauquelin, 75005 Paris, France
,
Katja S. Håheim
a   ESPCI Paris – PSL, CNRS, 10 Rue Vauquelin, 75005 Paris, France
,
Julien Boutet
b   Seqens SAS, 21 Chemin de la Sauvegarde, 21 Ecully Parc, Ecully 69130, France
,
Pierre Gilles
c   Proteus by Seqens, 70 Allée Graham Bell, Parc Georges Besse, 30035 Nîmes Cedex 1, France
,
Juliette Martin
c   Proteus by Seqens, 70 Allée Graham Bell, Parc Georges Besse, 30035 Nîmes Cedex 1, France
,
Janine Cossy
a   ESPCI Paris – PSL, CNRS, 10 Rue Vauquelin, 75005 Paris, France
› Institutsangaben


Abstract

Cross-coupling reactions have been developed between C2-substituted 1-bromocyclobut-1-enes and Grignard reagents using two effective catalysts, e.g., Fe(acac)3 and Ni(acac)2. The iron catalyst works in THF but requires NMP as the co-solvent, with the advantage of achieving cross-coupling reactions with alkyl Grignard reagents. The nickel catalyst was able to promote the reactions in THF without any additive and showed high reactivity with electron-rich aryl Grignard reagents. These catalysts gave various types of substituted cyclobutenes in good yields.

Supporting Information



Publikationsverlauf

Eingereicht: 31. Mai 2024

Angenommen nach Revision: 17. Juni 2024

Accepted Manuscript online:
17. Juni 2024

Artikel online veröffentlicht:
04. Juli 2024

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