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

Arnaud Boreux; Kiran Indukuri; Fabien Gagosz; Olivier Riant

doi:10.1021/acscatal.7b02938

Journal articles

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

Domain :

Chemical Sciences / Organic chemistry

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https://hal-polytechnique.archives-ouvertes.fr/hal-02090685
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Submitted on : Friday, April 5, 2019 - 9:32:13 AM
Last modification on : Friday, April 12, 2019 - 1:31:50 AM

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

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

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