Metal-free oxidative coupling of alkyl chlorides with thiols: An efficient access to sulfoxides

[Display omitted] •Step-economical synthesis.•Metal-free conditions.•Without super acid or base.•Simple and widely available starting materials.•Avoidance of over-oxidation. An efficient and step-economical access to sulfoxides from thiols and alkyl halides in the presence of I2O5 and DBU via direct...

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Bibliographic Details
Published in:Tetrahedron letters 2020-02, Vol.61 (7), p.151492, Article 151492
Main Authors: Liu, Qian, Zhao, Xiaoqian, Xu, Feng, Li, Gaoqiang
Format: Article
Language:English
Subjects:
Coupling
Metal-free
Oxidation
Sulfoxides
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Summary:[Display omitted] •Step-economical synthesis.•Metal-free conditions.•Without super acid or base.•Simple and widely available starting materials.•Avoidance of over-oxidation. An efficient and step-economical access to sulfoxides from thiols and alkyl halides in the presence of I2O5 and DBU via direct oxidative couplings is described here. It is the first case that combined Williamson sulfide synthesis and subsequent sulfide oxidation into one step manipulation for sulfoxides preparation. This protocol features wide substrate scope, mild and metal-free conditons, the use of naturally abundant starting materials and avoidance of over-oxidation.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.151492