Synthesis of enyne and aryl vinyl sulfoxides: functionalization via Pummerer rearrangement

An efficient methodology for the synthesis of aryl-substituted vinyl sulfoxides through direct substitution of aryl-substituted alkynyl grignard reagents on menthyl- p -toluenesulfinate followed by Suzuki–Miyaura cross-coupling reaction has been developed. It has also been described that the reactio...

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Bibliographic Details
Published in:Molecular diversity 2015-11, Vol.19 (4), p.773-785
Main Authors: Souza, Frederico B., Shamim, Anwar, Argomedo, Luiz M. Z., Pimenta, Daniel C., Stefani, Hélio A.
Format: Article
Language:English
Subjects:
Aldehydes - chemistry
Biochemistry
Biological diversity
Biomedical and Life Sciences
Full-Length Paper
Life Sciences
Molecular biology
Molecular Structure
Organic Chemistry
Pharmacy
Polymer Sciences
Stereoisomerism
Sulfoxides - chemical synthesis
Sulfoxides - chemistry
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Summary:An efficient methodology for the synthesis of aryl-substituted vinyl sulfoxides through direct substitution of aryl-substituted alkynyl grignard reagents on menthyl- p -toluenesulfinate followed by Suzuki–Miyaura cross-coupling reaction has been developed. It has also been described that the reaction of alkyl-substituted and cycloalkyl-substituted alkynyl grignard reagents with menthyl- p -toluenesulfinate led to two products, i.e., alkynyl sulfoxide derivatives, as a result of substitution, and enyne sulfoxide derivatives, which resulted from substitution followed by Michael type addition. It was possible to selectively synthesize the enyne sulfoxide derivatives by changing the concentration of the grignard reagent. These alkenyl sulfoxides were transformed into the corresponding α -thio aldehydes in high yields via additive Pummerer rearrangement.
ISSN:1381-1991
1573-501X
DOI:10.1007/s11030-015-9619-x