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New Catalytic Method for the Synthesis of β ‐Hydroxy Selenides
Author(s) -
Zhang Yikun,
Wu Sixue,
Yan Jie
Publication year - 2016
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201600115
Subject(s) - chemistry , catalysis , stereospecificity , electrophile , markovnikov's rule , cleavage (geology) , combinatorial chemistry , medicinal chemistry , electrophilic addition , in situ , oxidative cleavage , bond cleavage , stereochemistry , organic chemistry , regioselectivity , geotechnical engineering , fracture (geology) , engineering
In the presence of NH 4 I as catalyst and m ‐chloroperbenzoic acid as oxidant, the Se–Se bond cleavage of diselenides undergoes smoothly. The in situ generated reactive electrophilic Se species reacts with alkenes quickly, and a series of β ‐hydroxy selenides are prepared in good yields. This new catalytic method for synthesis of β ‐hydroxy selenides is a stereospecific anti addition, which occurs with a Markovnikov orientation.
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