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Selenolate Anion as an Organocatalyst: Reactions and Mechanistic Studies
Author(s) -
Trofymchuk Oleksandra S.,
Zheng Zhipeng,
Kurogi Takashi,
Mindiola Daniel J.,
Walsh Patrick J.
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201701568
Subject(s) - chemistry , selenide , diselenide , ion , diphenyl diselenide , organic chemistry , combinatorial chemistry , medicinal chemistry , selenium
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.