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Photoinduced Difunctionalization Of 2,3-Dihydrofurans

Posted on:2018-12-17Degree:MasterType:Thesis
Country:ChinaCandidate:X X ZhuFull Text:PDF
GTID:2321330515970078Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Multicomponent reactions combine at least three reactants in the same pot to generate a product containing most(preferably all)atoms of the starting materials.Their atom economy,efficiency,high convergence and mild conditions,with their general compatibility with green chemistry would justify a central place in the toolbox of sustainable synthetic methodologies.Very recenltly,photoredox catalysis has emerged as a powerful tool in synthetic chemistry,due to its intrinsic characteristics of mild,environmentally benign,operationally simple,infinitely available source.It is not surprising,that in the search for increasingly efficient and sustainable syntheses,chemists have started to look at the possibility to combine the special characteristics of multicomponent and photochemical approaches.Photoinduced multicomponent reactions are still in their infancy,but significant developments in this area are expected in the near future.Therefore,in this text,recent developments in photoredox catalysis area were reviewed and the related photoinduced MCRS were also presented follow:A high efficent photoinduced difunctionalization of 2,3-dihydrofurans and vinyl carboxylic acid with TBHP has been developed.The reaction proceed under the irradiation of 3 W blue LED in air for 16 h with of Ru(phen)3Cl2(2 mol %)as the photocatalyst,BI-OAc(30 mol %)as the additive and ethyl acetate as the solvent.A wide range of functional groups were tolerated and the corresponding products were obtained in high yields.Substituted tetrahydrofuran scaffolds are useful building blocks for the synthesis of modified nucleosides1 with high biological activities.Moreover,substituted tetrahydrofuran scaffolds are important structural motifs existing in many natural products and pharmaceuticals.This protocol has the new regioselectivity of olefin in 2,3-dihydrofuran and a plausible reaction mechanism through the energy transfer pathway has been proposed.
Keywords/Search Tags:multicomponent reactions, visible-light irradiation, difunctionalization, photocatalyst, hypervalent iodine(?) reagent
PDF Full Text Request
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