Stereoselective Electrochemical Synthesis of E-Tetrasubstituted Haloalkenyl Chalcogenides.

Autor: Lopes EF; Institute, of Chemistry, State University of Campinas - UNICAMP, PO Box 6154, 13083970, Campinas, SP, Brazil., Costa E Silva R; Institute, of Chemistry, State University of Campinas - UNICAMP, PO Box 6154, 13083970, Campinas, SP, Brazil., Souza RAC; Institute, of Chemistry, State University of Campinas - UNICAMP, PO Box 6154, 13083970, Campinas, SP, Brazil., Sebastian Fernandez P; Institute, of Chemistry, State University of Campinas - UNICAMP, PO Box 6154, 13083970, Campinas, SP, Brazil., Cezar Pastre J; Institute, of Chemistry, State University of Campinas - UNICAMP, PO Box 6154, 13083970, Campinas, SP, Brazil.
Jazyk: angličtina
Zdroj: Chemistry, an Asian journal [Chem Asian J] 2024 Dec 16; Vol. 19 (24), pp. e202400960. Date of Electronic Publication: 2024 Oct 31.
DOI: 10.1002/asia.202400960
Abstrakt: Herein, we describe an electrochemical method for the synthesis of haloalkenyl chalcogenides from internal alkynes using hydrobromic and hydrochloric acids as halogenating agents, with the sole byproduct being hydrogen gas. This e-halochalcogenation protocol generates electrophilic chalcogenium species under mild conditions in a simple, undivided cell setup, enabling the synthesis of 25 examples of chloro- and bromovinyl selenides and sulfides with yields ranging from 10 % to 94 %, predominantly as the E-isomer. The synthetic utility of the halovinyl chalcogenides was demonstrated through various transformations, yielding densely functionalized tetra-substituted olefins. This underscores the versatility and efficiency of our method in assembling intricate molecular frameworks.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
Externí odkaz: