Wittig Reagents as Metallocarbene Precursors: In Situ Generated Monocarbonyl Iodonium Ylides | Zendy

Ho Phyllis E. | Zendy; Tao Jason | Zendy; Murphy Graham K. | Zendy

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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.

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