Aqueous CB7/?-cyclodextrin Derivatives Catalyzed CuAAC Reaction

Supramolecular catalysis is a research direction that crosses green,organic and other chemical disciplines.In recent years,it has become one of the important research topics in the field of organic catalysis technology.Cyclodextrin has the advantages of a truncated cone-shaped cavity structure that is hydrophilic on the outside and hydrophobic on the inside,non-toxic,and modifiable.Because ?-cyclodextrin is cheap and easily available,?-cyclodextrin and its derivatives are widely used to catalyze organic reactions in the water phase.Cucurbit[n]uril has a special rigid space structure and a hydrophobic cavity,a symmetrical negatively charged carbonyl central port,which can coordinate with metal ions.Because CB7 has a moderate cavity and good water solubility,it is widely used in organic reactions catalyzed by aqueous metals.In order to further study the catalysis of cucurbit[n]uril and cyclodextrin derivatives,this article explored the catalytic performance of cucurbit[n]uril metal copper catalyst(CB7-CuI)in the CuAAC reaction.Due to the addition of CB7,the click cyclization reaction of various aryl azides and alkynes in water is accelerated,and the catalyst can be recycled.Secondly,this article also explored the catalytic activity of the triple cyclodextrin monovalent copper complex catalyst,The triple cyclodextrin monovalent copper complex catalyst can efficiently catalyze the CuAAC reaction to synthesize coumarin triazole compounds in water,and the catalyst can also be recycled.Therefore,the research content of this article is mainly divided into the following two parts:1.The effect of cucurbit[7]urea(CB7)and CuI co-catalyzing the CuAAC reaction was explored,and a more suitable catalytic condition for this reactant was found.The results show that CuI and CB7 can successfully accelerate the CuAAC reaction under the catalyst amount,and expand the synthesis of products to 34,and the yield is as high as 98 %.The co-catalyst can be recycled and reused,and the efficiency of multiple recycling applications can still be high.The advantages of this metal co-catalysis system not only fully meet the requirements of green chemistry,but also have potential industrial applications.2.The water-soluble claw-shaped triple cyclodextrin supramolecular metal copper catalyst was explored to catalyze the CuAAC reaction to synthesize coumarin triazole compounds,and a better catalytic condition was found.The results show that under 5 % of the catalytic amount,the CuAAC reaction can be successfully and efficiently catalyzed to synthesize coumarin triazole compounds within 2 h,and 12 coumarin triazole compounds with different substituents have been synthesized,and the yield is good Up to 99 %.The catalyst can also be recycled and still maintains high recycling catalytic activity.