Palladium-catalyzed tandem dimerization and cyclization of acetylenic ketones: a convenient method for 3,3'-bifurans using PdCl2(PPh3)2.
Alkynones undergo tandem dimerization and cyclization in the presence of PdCl2(PPh3)2 and triethylamine in tetrahydrofuran at room temperature to give 3,3'-bifurans predominantly. Other palladium catalysts while under similar conditions, by rearrangement, lead to 2,5-disubstituted furans. This distinguished property of PdCl2(PPh3)2 has been attributed to the involvement of hydridopalladium halide. This method provides a simpler route to a variety of furans and a regioselective synthesis of polysubstituted 3,3'-bifurans using easily accessible acetylenic ketones.
Jeevanandam
A
A
Department of Chemistry, National Tsing Hua University, Hsinchu, 30043, Taiwan.
Narkunan
K
K
Ling
Y C
YC
D018360:Crystallography, X-Ray; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D005663:Furans; D007659:Ketones; D009942:Organometallic Compounds; D010165:Palladium; C008756:palladium chloride