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

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

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2023-05, Vol.62 (19), p.e202300685
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 -alkynes with N, O and S-nucleophiles and further functionalization of the corresponding Z-(hetero)vinyl-SF intermediates, a suitable platform to access α-SF ketones and esters, β-SF amines and alcohols under mild reaction conditions. Experimental and computational comparative studies between SF - and CF -alkynes have been performed to highlight and explain the difference of reactivity and selectivity observed between these two fluorinated motifs.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202300685