Iron-Catalyzed Cross-Coupling Reactions between a Bicyclic Alkenyl Triflate and Grignard Reagents

Fe-catalyzed cross-coupling reactions between a bicyclic alkenyl triflate and Grignard reagents were investigated. Under the optimized reaction conditions, various 2-substituted bicyclic alkenes were synthesized in moderate to excellent yields (52−93%). This method provided an efficient route for th...

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Bibliographic Details
Published in:Journal of organic chemistry 2008-10, Vol.73 (19), p.7829-7832
Main Authors: Le Marquand, Paul, Tsui, Gavin C, Whitney, John C. C, Tam, William
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Alkenes
Alkylation
Bridged Bicyclo Compounds
Catalysis
Chemistry
Cross-Linking Reagents
Exact sciences and technology
Iron - chemistry
Mesylates - chemistry
Organic chemistry
Preparations and properties
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Summary:Fe-catalyzed cross-coupling reactions between a bicyclic alkenyl triflate and Grignard reagents were investigated. Under the optimized reaction conditions, various 2-substituted bicyclic alkenes were synthesized in moderate to excellent yields (52−93%). This method provided an efficient route for the synthesis of 2-substituted bicyclic alkenes with 2° alkyl groups which cannot be synthesized using previous methods such as Pd-catalyzed coupling reactions and lithium−halide exchange reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo801384e