A Practical and Catalytic Reductive Olefin Coupling

A redox-economic method for the direct coupling of olefins that uses an inexpensive iron catalyst and a silane reducing agent is reported. Thus, unactivated olefins can be joined directly to electron-deficient olefins in both intra- and intermolecular settings to generate hindered bicyclic systems,...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 136; no. 4; pp. 1304 - 1307
Main Authors Lo, Julian C, Yabe, Yuki, Baran, Phil S
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 29.01.2014
Amer Chemical Soc
Subjects
Alkenes - chemistry
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Communication
Coupling agents
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Iron
Joining
Moisture
Molecular Structure
Olefins
Organic compounds
Oxidation-Reduction
Physical Sciences
Science & Technology
Silanes
Stereoisomerism
ALKENES
CYCLIZATIONS
DITERPENOIDS
CONVENIENT
HYDROFLUORINATION
RADICALS
UNACTIVATED OLEFINS
HYDROHYDRAZINATION
CONJUGATE ADDITION
HYDROAZIDATION
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Summary:A redox-economic method for the direct coupling of olefins that uses an inexpensive iron catalyst and a silane reducing agent is reported. Thus, unactivated olefins can be joined directly to electron-deficient olefins in both intra- and intermolecular settings to generate hindered bicyclic systems, vicinal quaternary centers, and even cyclopropanes in good yield. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. Most importantly, it allows access to many compounds that would be difficult or perhaps impossible to access using other methods.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja4117632