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 the synthesis of 2-substituted bicyclic alkenes with secondary alkyl groups which cannot be synthesized using previous methods such as Pd-catalyzed coupling reactions and lithium-halide exchange reactions.
Le Marquand
Paul
P
Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1.
Tsui
Gavin C
GC
Whitney
John C C
JC
Tam
William
W
D000475:Alkenes; D000478:Alkylation; D001643:Bridged Bicyclo Compounds; D002384:Catalysis; D003432:Cross-Linking Reagents; D007501:Iron / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*
D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D003432:Cross-Linking Reagents; D008698:Mesylates; D007501:Iron; C012077:trifluoromethanesulfonic acid