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Wittig Reagents as Metallocarbene Precursors: In Situ Generated Monocarbonyl Iodonium Ylides
Author(s) -
Ho Phyllis E.,
Tao Jason,
Murphy Graham K.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300954
Subject(s) - wittig reaction , cyclopropanation , chemistry , phosphonium , reagent , catalysis , in situ , organic chemistry , combinatorial chemistry , photochemistry
A proof of concept study was undertaken to determine the suitability of monocarbonyl iodonium ylides (MCIYs) as metallocarbene precursors. Exposing Wittig reagents to iodosylbenzene results in a pseudo‐Wittig reaction that generates MCIYs in situ. These ylides are intercepted by transition‐metal catalysts to generate metallocarbenes, which then undergo either dimerization or cyclopropanation reactions with a variety of alkenes. Additionally, the reaction between diazoester‐derived metallocarbenes and Wittig reagents afforded cross‐coupling products, illustrating a new type of olefination reaction for phosphonium ylides.