Synthesis Of Indene Derivative By Pd?oac?₂-catalyzed Baylis-hillman Adducts

Benzo cyclic compounds are widely present in natural products.Indene compounds are an important class of benzo cyclic compounds,they have good biological disinfection,anticoagulant and anti-tumor activity.Indene derivatives are important structural moieties found in various functional materials and biologically active molecules.Baylis-Hillman adducts is one kind of new stereocenters and has proven to be a very useful carbon-carbon bond-forming method in the synthesis of highly functionalized molecules.Palladium-catalyzed chemical transformations of modified Baylis-Hillman adducts started very recently,but have already provided many good results.This dissertation has made collective references on the synthesis methods of Indene,Baylis-Hillman reaction,the palladium-catalyzed reactions of Baylis-Hillman adducts,the palladium-catalyzed intermolecular C-H activation,the palladium-catalyzed intramolecular C-H activation,the palladium-catalyzed cyclization reaction,the palladium-catalyzed synthesis of indene.After experimental study,we successfully developed a method of synthesis of indene derivatives by palladium-catalyzed Baylis-Hillman adducts.Part 1:we make use of methyl acrylate and various substituted benzaldehyde as raw,25 Baylis-Hillman adducts of acetate were synthesized in good yields by Baylis-Hillman reaction and acetylation.Part 2:22 Indene derivatives were obtained by cyclization of Baylis-Hillman adducts of acetate in the presence of Pd(OAc)2.The reaction was taken under reflux condition with 1,4-Dioxane as the sl vent for 10h.5 mol%Pd(OAc)2 as the catalyst?lequiv K2CO3 as base,PPh3 as the ligand.This cyclization reaction shows some advantages in terms of its simple operation,easily available and afford the products in moderate good yield.In addition,we also study the limitations and selectivity of the reaction,verify the reaction mechanism.In conclusion,we developed a concise method of cyclization reactions of Baylis-Hillman adducts catalyzed by Pd(OAc)2.These method expand the application of Baylis-Hillman adducts and the palladium-catalyzed reactions in the organic chemistry.