37985-11-8Relevant articles and documents
A NOVEL SYNTHESIS OF (E,E)-1,4-DIARYL-1,3-BUTADIENES BY THE RUTHENIUM(II) CATALYZED REACTION OF (E)-2-ARYLETHENESULFONYL CHLORIDES WITH VINYLARENES
Kamigata, Nobumasa,Ozaki, Jun-ichi,Kobayashi, Michio
, p. 705 - 708 (1985)
Symmetrical and unsymmetrical (E,E)-1,4-diaryl-1,3-butadienes can be prepared in high yields from (E)-2-arylethenesulfonyl chlorides by treating with vinylarenes in the presence of ruthenium(II) phosphine complex in benzene.
Synthesis of stilbene derivatives via visible-light-induced cross-coupling of aryl diazonium salts with nitroalkenes using-NO2 as a leaving group
Zhang, Na,Quan, Zheng-Jun,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
supporting information, p. 14234 - 14237 (2016/12/14)
The straightforward visible-light-induced synthesis of stilbene compounds via the cross-coupling of nitroalkenes and diazonium tetrafluoroborates under transition-metal-free conditions is described. The protocol uses green LEDs as light sources and eosin Y as an organophotoredox catalyst. Broad substrate scope and exclusive selectivity for the (E)-configuration of stilbenes are observed. This protocol proceeds via a radical pathway, with nitroalkenes serving as the radical acceptor, and the nitro group is cleaved during the process.
Wittig reaction with ion-supported Ph3P
Shimojuh, Naoya,Imura, Yumi,Moriyama, Katsuhiko,Togo, Hideo
experimental part, p. 951 - 957 (2011/03/18)
Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide A and N-methyl-N-[4-(diphenylphosphino)benzyl]pyrrolidinium bromide B, were used for the Wittig reaction. Ion-supported phosphonium salts A1 and B1, which were prepared from the reactions of ion-supported Ph3P A and B with ethyl bromoacetate, respectively, reacted with aromatic and aliphatic aldehydes in the presence of K2CO3 to give the corresponding α,β-unsaturated ethyl esters in good yields with high purity by simple filtration of the reaction mixture and subsequent removal of the solvent from the filtrate. Similarly, ion-supported phosphonium salts A2 and B2, which were prepared from the reactions of ion-supported Ph3P A and B with p-methylbenzyl bromide, respectively, reacted with aromatic and aliphatic aldehydes in the presence of NaH to provide the corresponding p-methylstyrene derivatives in good yields with high purity by simple filtration of the reaction mixture and the subsequent removal of the solvent from the filtrate. In both reactions, the co-product, ion-supported Ph3PO, could be obtained quantitatively by simple filtration, and was converted into the corresponding ion-supported Ph3P A and B again in high yields using dimethyl sulfate, followed by the reduction with LiAlH4. Recovered and regenerated ion-supported Ph3P A and B could be reused for the same Wittig reaction while maintaining good yields of ethyl (E)-3-(4′-chlorophenyl)-2-propenoate and 1-(4′-chlorophenyl)-2- (4″-methylphenyl)ethene with high purity by simple filtration and removal of the solvent from the filtrate.