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 in:Journal of the American Chemical Society 2014-01, Vol.136 (4), p.1304-1307
Main Authors: Lo, Julian C, Yabe, Yuki, Baran, Phil S
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Catalysis
Catalysts
Communication
Coupling agents
Cyclopropanes - chemical synthesis
Cyclopropanes - chemistry
Iron
Joining
Moisture
Molecular Structure
Olefins
Organic compounds
Oxidation-Reduction
Silanes
Stereoisomerism
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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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja4117632