The chemoselective synthesis of trisubstituted alkenyl halides (Cl, Br, F, I) starting from ketones and aldehydes and lithum halocarbenoids is reported. Upon forming the corresponding tetrahedral intermediate adduct, followed by the addition of thionyl chloride, a selective E2-type elimination is triggered, thus furnishing the targeted motifs. The transformation takes place under full chemocontrol: various sensitive functionalities (e.g. ester, nitrile, nitro, halogen groups) can be placed on the starting materials, thus documenting a wide reaction scope, as well as, the application of the technique to biologically active substances.
Chemoselective Homologative Preparation of Trisubstituted Alkenyl Halides from Carbonyls and Carbenoids / M. Miele, D. Castiglione, W. Holzer, L. Castoldi, V. Pace. - In: CHEMICAL COMMUNICATIONS. - ISSN 1364-548X. - (2024), pp. 1-6. [Epub ahead of print] [10.1039/D4CC05937A]
Chemoselective Homologative Preparation of Trisubstituted Alkenyl Halides from Carbonyls and Carbenoids
L. Castoldi
;
2024
Abstract
The chemoselective synthesis of trisubstituted alkenyl halides (Cl, Br, F, I) starting from ketones and aldehydes and lithum halocarbenoids is reported. Upon forming the corresponding tetrahedral intermediate adduct, followed by the addition of thionyl chloride, a selective E2-type elimination is triggered, thus furnishing the targeted motifs. The transformation takes place under full chemocontrol: various sensitive functionalities (e.g. ester, nitrile, nitro, halogen groups) can be placed on the starting materials, thus documenting a wide reaction scope, as well as, the application of the technique to biologically active substances.File | Dimensione | Formato | |
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