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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of beta-Keto Thioethers

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Author(s):
Dias, Rafael M. P. [1] ; Burtoloso, Antonio C. B. [1]
Total Authors: 2
Affiliation:
[1] Univ Sao Paulo, Inst Quim Sao Carlos, BR-13560970 Sao Carlos, SP - Brazil
Total Affiliations: 1
Document type: Journal article
Source: ORGANIC LETTERS; v. 18, n. 12, p. 3034-3037, JUN 17 2016.
Web of Science Citations: 31
Abstract

Insertion of sulfoxonium ylides into the S-H bond of aryl thiols without the need for a catalyst is demonstrated, furnishing beta-keto thioethers in excellent yield in most cases. The method overcomes traditional syntheses that employ metal catalysts in combination with diazo compounds or toxic and hard-prepared haloketones. The experimental setup consists of mixing the reagents in acetonitrile at room temperature. Additional experimental as well as kinetic isotopic effect studies give some insight into the mechanism of this reaction. (AU)

FAPESP's process: 13/18009-4 - Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors
Grantee:Carlos Alberto Montanari
Support type: Research Projects - Thematic Grants
FAPESP's process: 13/25504-1 - Development of new methodologies for the asymmetric a-functionalization of carbonyl compounds using chiral catalysts
Grantee:Antonio Carlos Bender Burtoloso
Support type: Regular Research Grants