Stereoselective Electrochemical Synthesis of E-Tetrasubstituted Haloalkenyl Chalcogenides

Author(s)

Lopes, Eric F. ; Costa e Silva, Rodrigo ; Souza, Rafael A. C. ; Fernandez, Pablo Sebastian ; Pastre, Julio Cezar

• Document type: Journal article
• Source: CHEMISTRY-AN ASIAN JOURNAL; v. N/A, p. 8-pg., 2024-10-31.

Abstract

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. (AU)

• FAPESP's process: 23/07466-7 - Development of Self-Optimization Platforms for the Multi-Step Synthesis of APIs
• Grantee: Rodrigo Costa e Silva
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 23/02929-9 - Boosting green hydrogen production by the electrooxidation of glycerol. Minimizing the use of Platinum Group Metals elements
• Grantee: Pablo Sebastián Fernández
• Support Opportunities: Regular Research Grants
• FAPESP's process: 23/01930-3 - Conversion of biomass derivatives to high value materials and green solvents for high valuable chemicals
• Grantee: Eric Francis Lopes
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 21/06661-5 - Enabling technologies for the sustainable chemical synthesis of platform molecules, new chemicals and bioactive compounds
• Grantee: Júlio Cezar Pastre
• Support Opportunities: Program for Research on Bioenergy (BIOEN) - Young Investigators Grants - Phase 2
• FAPESP's process: 17/11986-5 - Generation and storage of New Energy: bringing technological development for the country
• Grantee: Ana Flávia Nogueira
• Support Opportunities: Research Grants - Research Centers in Engineering Program