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Hypoiodite‐Mediated Catalytic Cyclopropanation of Alkenes with Malononitrile
Author(s) -
Yoshimura Akira,
Jones T. Nicholas,
Yusubov Mekhman S.,
Zhdankin Viktor V.
Publication year - 2014
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.201400627
Subject(s) - cyclopropanation , chemistry , catalysis , malononitrile , aryl , organic chemistry , iodine , combinatorial chemistry , alkyl
An efficient synthetic procedure for dicyano‐cyclopropanation of alkenes using catalytic amounts of molecular iodine as a precatalyst and tert ‐butyl hydroperoxide (TBHP) as a terminal oxidant under mild conditions has been developed. This catalytic reaction works especially well for the aryl‐substituted double bond affording products of cyclopropanation in high yields. A catalytic cycle based on the generated in situ hypoiodite species has been proposed.