Regio‐ and Stereoselective Hydroelementation of SF 5 ‐Alkynes and Further Functionalizations

Herein is described a fully regio‐ and stereoselective hydroelementation reaction of SF 5 ‐alkynes with N, O and S‐nucleophiles and further functionalization of the corresponding Z ‐(hetero)vinyl‐SF 5 intermediates, a suitable platform to access α‐SF 5 ketones and esters, β‐SF 5 amines and alcohols...

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Bibliographic Details
Published in:Angewandte Chemie 2023-05, Vol.135 (19)
Main Authors: Popek, Lucas, Cabrera‐Trujillo, Jorge Juan, Debrauwer, Vincent, Blanchard, Nicolas, Miqueu, Karinne, Bizet, Vincent
Format: Article
Language:English
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Summary:Herein is described a fully regio‐ and stereoselective hydroelementation reaction of SF 5 ‐alkynes with N, O and S‐nucleophiles and further functionalization of the corresponding Z ‐(hetero)vinyl‐SF 5 intermediates, a suitable platform to access α‐SF 5 ketones and esters, β‐SF 5 amines and alcohols under mild reaction conditions. Experimental and computational comparative studies between SF 5 ‐ and CF 3 ‐alkynes have been performed to highlight and explain the difference of reactivity and selectivity observed between these two fluorinated motifs.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202300685