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

Mol Divers

Departamento de Farmácia, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, SP, Brazil.

Published: November 2015

AI Article Synopsis

  • A new process has been created to synthesize aryl-substituted vinyl sulfoxides using aryl-substituted alkynyl Grignard reagents and menthyl-p-toluenesulfinate with a Suzuki-Miyaura cross-coupling step.
  • The methodology produced two types of products from alkyl- and cycloalkyl-substituted alkynyl Grignard reagents: alkynyl sulfoxide derivatives from substitution and enyne sulfoxide derivatives from substitution followed by Michael addition.
  • By adjusting the concentration of the Grignard reagent, researchers could selectively produce the enyne sulfoxide derivatives, which were then efficiently converted into [Formula: see text]-thio alde

Article Abstract

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 [Formula: see text]-thio aldehydes in high yields via additive Pummerer rearrangement.

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Source
http://dx.doi.org/10.1007/s11030-015-9619-xDOI Listing

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