Synthesis of beta-lactones: a highly active and selective catalyst for epoxide carbonylation.
A new highly active and selective catalyst for the synthesis of beta-lactones from CO and epoxides is reported. The catalyst, [(N,N'-bis(3,5-di-tert-butylsalicylidene) phenylenediamino)Al(THF)2][Co(CO)4] ([(salph)Al(THF)2][Co(CO)4]) is easily prepared from the corresponding (salph)AlCl and NaCo(CO)4. At 50 degrees C and 880 psi of CO, the catalyst (1 mol %) carbonylates epoxides such as propylene oxide, 1-butene oxide, epichlorohydrin, and isobutylene oxide to the lactones beta-butyrolactone, beta-valerolactone, gamma-chloro-beta-butyrolactone, and beta-methyl-beta-butyrolactone in high yield. (R)-Propylene oxide was carbonylated to (R)-beta-butyrolactone with retention of stereochemistry.
Getzler
Yutan D Y L
YD
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853, USA.
Mahadevan
Viswanath
V
Lobkovsky
Emil B
EB
Coates
Geoffrey W
GW
D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D006885:Hydroxybutyrates / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D011091:Polyesters / Q000737:chemistry; D000094122:Polyhydroxybutyrates
D003035:Cobalt; D004852:Epoxy Compounds; D006885:Hydroxybutyrates; D007783:Lactones; D011091:Polyesters; C003182:poly-beta-hydroxybutyrate; D000094122:Polyhydroxybutyrates