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1、6302Chem.Rev.2010,110,63026337Water:Nature’sReactionEnforcersComparativeEffectsforOrganicSynthesis“In-Water”and“On-Water”,,RichardN.Butler*andAnthonyG.Coyne*SchoolofChemistry,NationalUniversityofIreland,UniversityRoad,Galway,Ireland,andDepartmentofChemistry,UniversityofCa
2、mbridge,LensfieldRoad,Cambridge,CB21EW,UnitedKingdomReceivedMay28,2010Contents1.Introduction1.Introduction6302Wateristhesolventusedbynatureforbiological2.WaterEffectsonOrganicReactions6303chemistry.Consideringtheenormousvarietyofbiologicalorganicsyntheticpathwaysandthecomp
3、licatedmolecular2.1.In-Water6303structuresandmaterials,includingprecisearrangementsof2.1.1.TheBreslowHydrophobicEffect6303multitudesofasymmetriccenters,whicharefoundin2.1.2.Hydrogen-BondingEffect6304biologicalsystems,itisremarkablethatupuntilrecentlyin2.1.3.PolarityEffect
4、6307vitroorganicsynthesishasmainlyshunnedwaterand2.2.OnWater6308chemistsandindustrieshavebeensearchingforacceptable2.2.1.On-WaterReactions.Marcustrans-Phase6308organicsolvents,forexample,thereplacementoftheearlierH-Bondingwidelyusedbenzenewithtoluene,etc.Generationsof2.2.
5、2.Insolubility.SolidsvsLiquids.The6309organicchemistshavebeentrainedinsuchamannerthaton-WaterLimit(SeeSupportinglittleseriousconsiderationwasgiventowaterasausefulInformation)reactionsolvent.Thiswasprobablypartlytheresultofa3.SyntheticReactions6311combinationoffearofthedet
6、rimentaleffectsofhydrolysis3.1.PericyclicReactions6311andtheinfluenceoftheancientalchimia,whichteachesthat3.1.1.Diels-Alder[4+2]Cycloaddition6311reactantsmustbeinsolutiontoproduceachemicalreaction.ReactionThesituationhasbeenchangingbecauseoftheearlywork3.1.2.Huisgen[3+2]Cy
7、cloadditionReaction6313ofBreslow1showinghowwaterenhancestheDiels-Alder3.1.3.ClaisenRearrangement6315reactions,oneofthefirstcasesofwhichwasoriginallyreportedusingwaterasareactionmedium.1,2Thesubsequent3.2.MulticomponentReactions63163.3.NucleophilicRing-OpeningReactions6316e
8、xplorationofthehydrophobiceffectinorganicreactions3.4.WittigReaction6318bytheBreslowgroupgreatly
