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Regio‐ and Stereoselective Hydroelementation of SF5‐Alkynes and Further Functionalizations
Herein is described a fully regio‐ and stereoselective hydroelementation reaction of SF5‐alkynes with N, O and S‐nucleophiles and further functionalization of the corresponding Z‐(hetero)vinyl‐SF5 intermediates, a suitable platform to access α‐SF5 ketones and esters, β‐SF5 amines and alcohols under...
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Published in: | Angewandte Chemie International Edition 2023-05, Vol.62 (19), p.e202300685-n/a |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Online Access: | Get full text |
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Summary: | Herein is described a fully regio‐ and stereoselective hydroelementation reaction of SF5‐alkynes with N, O and S‐nucleophiles and further functionalization of the corresponding Z‐(hetero)vinyl‐SF5 intermediates, a suitable platform to access α‐SF5 ketones and esters, β‐SF5 amines and alcohols under mild reaction conditions. Experimental and computational comparative studies between SF5‐ and CF3‐alkynes have been performed to highlight and explain the difference of reactivity and selectivity observed between these two fluorinated motifs.
Herein, fully regio‐ and stereoselective hydroamination, hydroetherification and hydrothioetherification reactions of SF5‐alkynes and further functionalizations of the corresponding Z‐(hetero)vinyl‐SF5 intermediates towards α‐SF5‐ketones, α‐SF5‐esters and β‐SF5‐amines are described. Experimental and computational comparative studies with CF3‐alkynes are also discussed. |
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ISSN: | 1433-7851 1521-3773 |
DOI: | 10.1002/anie.202300685 |