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Selenomethoxylation of Alkenes Promoted by Oxone®
Author(s) -
Perin Gelson,
Santoni Paolo,
Barcellos Angelita M.,
Nobre Patrick C.,
Jacob Raquel G.,
Lenardão Eder J.,
Santi Claudio
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701775
Subject(s) - chemistry , electrophile , methanol , solvent , selenium , stoichiometry , nucleophile , organic chemistry , reaction conditions , catalysis
We describe herein an alternative method for the selenomethoxylation of unactivated alkenes using Oxone® as a stoichiometric oxidant. The electrophilic species of selenium were easily generated in situ by the reaction of diorganyl diselenides with Oxone®. By this efficient and simple approach, β‐methoxy‐selenides were obtained in moderate to excellent yields at room temperature in an open flask, starting from alkenes by using methanol as both nucleophile and solvent. When a mixture of H 2 O/CH 3 CN was employed as the solvent, β‐hydroxy‐selenides were selectively obtained under mild conditions.