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PhI Catalyzed Acetoxyselenylation and Formyloxyselenylation of Alkenes
Author(s) -
Zhang Yikun,
Wu Sixue,
Yan Jie
Publication year - 2017
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.201600306
Subject(s) - hypervalent molecule , chemistry , regioselectivity , catalysis , electrophile , selenium , iodine , bond cleavage , cleavage (geology) , medicinal chemistry , oxidative cleavage , electrophilic addition , combinatorial chemistry , organic chemistry , stereochemistry , geotechnical engineering , fracture (geology) , engineering
With PhI as catalyst and m CPBA as oxidant, a novel and efficient catalytic procedure has been developed for the acetoxyselenylation and formyloxyselenylation of alkenes. In this protocol, PhI is first oxidized into hypervalent iodine intermediate, which promotes the cleavage of Se–Se bond in diselenides. The in situ generated electrophilic selenium species then reacts with alkenes, affording 2‐acetoxy‐1‐selenides and 2‐formyloxy‐1‐selenides in high regioselectivity and good yields.