Acyl Fluorides as Efficient Electrophiles for the Copper-Catalyzed Boroacylation of Allenes

Arnaud Boreux 1, 2 Kiran Indukuri 2 Fabien Gagosz 1, 3, * Olivier Riant 2, *
* Corresponding author
1 DCSO - Laboratoire de synthèse organique
2 IMCN/MOST Institute of Condensed Matter and Nanosciences, Molecules, Solids, Reactivity
3 Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall
Abstract : The copper-catalyzed reaction of allenes with bis(pinacolato)diboron and acyl electrophiles is reported. In this transformation, acyl fluorides have been proven to be more efficient coupling partners than their chloride or carboxylate analogues. The optimized reaction conditions employed were shown to be compatible with a range of commonly used functional groups, thereby allowing the formation of a library of β-boryl β,γ-unsaturated ketones by varying the nature of the allene and acyl fluoride substrates.
Keywords : acyl fluoride allene boration copper catalysis vinylboron
Document type :
Journal articles
Complete list of metadatas
https://hal-polytechnique.archives-ouvertes.fr/hal-02090685
Contributor : Aurélien Arnoux <>
Submitted on : Friday, April 5, 2019 - 9:32:13 AM
Last modification on : Friday, April 12, 2019 - 1:31:50 AM

Licence

Copyright

Identifiers

Collections

X | CNRS | X-DCSO | INC-CNRS | X-DEP-CHIM | UNIV-PARIS-SACLAY

Citation

Arnaud Boreux, Kiran Indukuri, Fabien Gagosz, Olivier Riant. Acyl Fluorides as Efficient Electrophiles for the Copper-Catalyzed Boroacylation of Allenes. ACS Catalysis, American Chemical Society, 2017, 7 (12), pp.8200-8204. ⟨10.1021/acscatal.7b02938⟩. ⟨hal-02090685⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

26

Contact

Informations

CCSD