Visible-Light-Promoted Selenofunctionalization of Alkenes

A visible-light-promoted method for the selenofunctionalization (and tellurofunctionalization) of alkenes has been developed. This method obviates the prepreparation of moisture-sensitive chalcogen electrophiles. The experimental setup is simple, and superior yields are obtained in the case of selen...

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Bibliographic Details
Published inOrganic letters Vol. 15; no. 21; pp. 5558 - 5561
Main Authors Conner, Elizabeth S, Crocker, Katherine E, Fernando, Ranelka G, Fronczek, Frank R, Stanley, George G, Ragains, Justin R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 01.11.2013
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
GAMMA-LYCORANE
ALCOHOLS
PHENYLSELENOLACTONIZATION
CYCLOFUNCTIONALIZATION
ELECTROCHEMICAL CYCLIZATION
RADICAL CYCLIZATION
OLEFINS
SELENIUM
UNSATURATED HYDROXY COMPOUNDS
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Summary:A visible-light-promoted method for the selenofunctionalization (and tellurofunctionalization) of alkenes has been developed. This method obviates the prepreparation of moisture-sensitive chalcogen electrophiles. The experimental setup is simple, and superior yields are obtained in the case of selenofunctionalization (up to 99%) while moderate to good yields are obtained in the case of tellurofunctionalization (53–75%). A variety of intra- and intermolecular processes and a short synthesis of the Amaryllidaceae alkaloid (±)-γ-lycorane are demonstrated with this method.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol402753u