Double Sulfur-Michael Addition Of Dienone With Thiol(Phenol) Catalyzed By Proline

The organic sulfur compounds have a wide range of applications in the fields of life sciences,synthetic pharmaceutical chemistry and natural pharmaceutical chemistry.The sulfur-Michael addition of sulfur-containing nucleophilic reagents with Michael receptors has proven to be the most powerful strategy in constructing the sulfur-carbon bond.It is an important organic reaction and can be used for the preparation of various types of sulfur-containing organic compounds.1,4-pentadiene-3-ketones(diene ketones)are a kind of good double Michael receptors,which can achieve two Michael addition reactions in one system and greatly improve the synthesis efficiency.Twelve 1,4-pentadiene-3-ketone Michael receptors with symmetrical structure were synthesized from substituted aromatic aldehydes and acetone by aldol condensation reaction.However,four 1,4-pentadiene-3-ketone Michael receptors with asymmetric structure were synthesized by two steps.The structure of target product was characterized by ~1H NMR after simple separation.The double sulfur-Michael addition of dienone with thiol(phenol)was investigated.Firstly,the reaction conditions such as catalyst,solvent,temperature,the amount of catalyst and material ratio were studied,and the optimized reaction conditions were determined.Under the optimized conditions,19 sulfur-containing organic compounds with different substituent were synthesized with high yield and moderate to high stereoselectivity,and the structure of the target products was determined.After that,the reaction mechanism was briefly deduced based on the experimental results.Finally,the amplification experiment was carried out and its application value was discussed.The study realized the efficient construction of two carbon sulfur bonds in a reaction process.It was provided an effective method for the synthesis of sulfur-containing organic compounds,and established foundation to expanding their potential applications in biomedicine and other fields.