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Direct Synthesis of ?-Sulfenylated Ketones under Electrochemical Conditions br

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Author(s):
de Souza, Aline A. N. ; Bartolomeu, Aloisio de A. ; Brocksom, Timothy J. ; Noel, Timothy ; de Oliveira, Kleber T.
Total Authors: 5
Document type: Journal article
Source: Journal of Organic Chemistry; v. 87, n. 9, p. 10-pg., 2022-05-06.
Abstract

We investigated the electrochemical sulfenylationreaction in both batch and continuousflow regimes, involvingthiophenols/thiols and enol-acetates to yield alpha-sulfenylatedketones, without using additional oxidants or catalysts. Studieswith different electrolytes were also performed, revealing thatquaternary ammonium salts are the best mediators for this reaction.Notably, during the study of the reaction scope, a Boc-cysteineproved to be extremely tolerant to our protocol, thus increasing itsrelevance. The methodology also proved to be scalable in bothbatch and continuousflow conditions, opening up possibilities forfurther studies since these relevant functional groups are important moieties in organic synthesis (AU)

FAPESP's process: 15/11801-0 - Development of flow chemistry synthetic platform to obtain molecules of pharmaceutical interest
Grantee:Leandro de Carvalho Alves
Support Opportunities: Research Grants - Innovative Research in Small Business - PIPE
FAPESP's process: 19/27176-8 - Asymmetric photocatalysis applied to the synthesis of Brivaracetam: synthetic approaches employing enabling technologies for chemical synthesis
Grantee:Kleber Thiago de Oliveira
Support Opportunities: Regular Research Grants
FAPESP's process: 13/07276-1 - CEPOF - Optics and Photonic Research Center
Grantee:Vanderlei Salvador Bagnato
Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
FAPESP's process: 20/06874-6 - Applications of technologies and synthetic methodologies developed under continuous flow conditions at LQBO-UFSCar for the preparation of molecules with biological activities and APIs
Grantee:Kleber Thiago de Oliveira
Support Opportunities: Regular Research Grants