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Ultrasound-promoted synthesis of 2-organoselanyl-naphthalenes using Oxone® in aqueous medium as an oxidizing agent.


ABSTRACT: A green methodology to synthesize 2-organoselanyl-naphthalenes based on the reaction of alkynols with diaryl diselenides is described. The electrophilic species of selenium were generated in situ, by the oxidative cleavage of the Se-Se bond of diaryl diselenides by Oxone® using water as the solvent. The reactions proceeded efficiently under ultrasonic irradiation as an alternative energy source, using a range of alkynols and diorganyl diselenides as starting materials. Through this methodology, the corresponding 2-organoselanyl-naphthalenes were obtained in moderate to good yields (56-94%) and in short reaction times (0.25-2.3 h).

SUBMITTER: Perin G 

PROVIDER: S-EPMC5944430 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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Ultrasound-promoted synthesis of 2-organoselanyl-naphthalenes using Oxone<sup>®</sup> in aqueous medium as an oxidizing agent.

Perin Gelson G   Araujo Daniela Rodrigues DR   Nobre Patrick Carvalho PC   Lenardao Eder João EJ   Jacob Raquel Guimarães RG   Silva Marcio Santos MS   Roehrs Juliano Alex JA  

PeerJ 20180507


A green methodology to synthesize 2-organoselanyl-naphthalenes based on the reaction of alkynols with diaryl diselenides is described. The electrophilic species of selenium were generated in situ, by the oxidative cleavage of the Se-Se bond of diaryl diselenides by Oxone<sup>®</sup> using water as the solvent. The reactions proceeded efficiently under ultrasonic irradiation as an alternative energy source, using a range of alkynols and diorganyl diselenides as starting materials. Through this me  ...[more]

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