Selenolate Anion as an Organocatalyst: Reactions and Mechanistic Studies

A new organocatalyst, the selenolate anion [RSe]–, generated from bench‐stable and commercially available diphenyl diselenide or from phenyl benzyl selenide (10 mol%) is introduced. Benchmarking is performed in the conversion of benzylic chlorides into trans‐stilbenes selectively at room temperature...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-04, Vol.360 (8), p.1685-1692
Main Authors: Trofymchuk, Oleksandra S., Zheng, Zhipeng, Kurogi, Takashi, Mindiola, Daniel J., Walsh, Patrick J.
Format: Article
Language:English
Subjects:
Anions
Organocatalyst
Screening
Selenium
Selenolate anion
Substrate
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Summary:A new organocatalyst, the selenolate anion [RSe]–, generated from bench‐stable and commercially available diphenyl diselenide or from phenyl benzyl selenide (10 mol%) is introduced. Benchmarking is performed in the conversion of benzylic chlorides into trans‐stilbenes selectively at room temperature. Mechanistic studies support the intermediacy of the selenolate anion and of 1,2‐diphenylethyl phenyl selenide.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201701568