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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| Published in | Organic letters Vol. 15; no. 21; pp. 5558 - 5561 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.11.2013
Amer Chemical Soc |
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| Abstract | 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. |
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| AbstractList | 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 (+/-)-gamma-lycorane are demonstrated with this method. 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. |
| Author | Fronczek, Frank R Ragains, Justin R Conner, Elizabeth S Crocker, Katherine E Stanley, George G Fernando, Ranelka G |
| AuthorAffiliation | Louisiana State University |
| AuthorAffiliation_xml | – name: Louisiana State University |
| Author_xml | – sequence: 1 givenname: Elizabeth S surname: Conner fullname: Conner, Elizabeth S – sequence: 2 givenname: Katherine E surname: Crocker fullname: Crocker, Katherine E – sequence: 3 givenname: Ranelka G surname: Fernando fullname: Fernando, Ranelka G – sequence: 4 givenname: Frank R surname: Fronczek fullname: Fronczek, Frank R – sequence: 5 givenname: George G surname: Stanley fullname: Stanley, George G – sequence: 6 givenname: Justin R surname: Ragains fullname: Ragains, Justin R email: jragains@lsu.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24134120$$D View this record in MEDLINE/PubMed |
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| Keywords | GAMMA-LYCORANE ALCOHOLS PHENYLSELENOLACTONIZATION CYCLOFUNCTIONALIZATION ELECTROCHEMICAL CYCLIZATION RADICAL CYCLIZATION OLEFINS SELENIUM UNSATURATED HYDROXY COMPOUNDS |
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| Snippet | A visible-light-promoted method for the selenofunctionalization (and tellurofunctionalization) of alkenes has been developed. This method obviates the... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Visible-Light-Promoted Selenofunctionalization of Alkenes |
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