Cycloisomerization of acetylenic acids to γ-alkylidene lactones using a palladium(II) catalyst supported on amino-functionalized siliceous mesocellular foam.
Cycloisomerization of various γ-acetylenic acids to their corresponding γ-alkylidene lactones by the use of a heterogeneous Pd(II) catalyst supported on amino-functionalized siliceous mesocellular foam is described. Substrates containing terminal as well as internal alkynes were cyclized in high to excellent yields within 2–24 h under mild reaction conditions. The protocol exhibited high regio- and stereoselectivity, favoring the exo-dig product with high Z selectivity. Moreover, the catalyst displayed excellent stability under the employed reaction conditions, as demonstrated by its good recyclability and low leaching.
Anuja
A
Nagendiran
Oscar
O
Verho
Clémence
C
Haller
Eric V
EV
Johnston
Jan-E
JE
Bäckvall
D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry*; D013237:Stereoisomerism
D000480:Alkynes; D000588:Amines; D007783:Lactones; D010165:Palladium; D012822:Silicon Dioxide