An efficient and selective aerobic oxidation of sulfides

An efficient and selective aerobic oxidation of sulfides

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1、TETRAHEDRONLETTERSPergamonTetrahedronLetters42(2001)71477151AnefficientandselectiveaerobicoxidationofsulfidestosulfoxidescatalyzedbyFe(NO3)3–FeBr3SandraE.Martı´n*andLauraI.RossiINFIQC,DepartamentodeQuı´micaOrga´nica,FacultaddeCienciasQuı´micas,UniversidadNacionaldeCo´rdoba,CiudadUniversi

2、taria,5000Co´rdoba,ArgentinaReceived10April2001;revised11August2001;accepted13August2001Abstract—ThebinarysystemFe(NO3)3FeBr3isaveryefficientcatalystfortheselectiveair-oxidationofsulfidestosulfoxides.Sincetheoxidationisselective,itmaybeappliedtoanytypeofdialkylandalkylarylsulfide,aswellas

3、tosubstratesofbiologicalinterest.Itdevelopsinmildconditions,givingahighyieldinthepresenceofdifferentfunctionalgroupsonthesulfide.OtherbinarysystemssuchasFe(NO3)3FeBr2andCu(NO3)2CuBr2arealsoeffectivecatalystsforsulfoxidation.Incontrasttopreviousoxygenationmethods,thisoxidationrequiresnei

4、theranaldehydenoratransitionmetalcomplex.©2001ElsevierScienceLtd.Allrightsreserved.Theoxidationofsulfidestosulfoxideshasbeentheaimincludingdioxygenoxidationcatalyzedbyeitherapal-ofconsiderableresearchduetotheimportanceofsul-910ladiumcomplex,oracomplexofRu(III),anddioxy-foxidesasusefulin

5、termediatesinorganicsynthesisandgenandaldehydes,11havebeendeveloped.Althoughthekeyrolessomeofthemplayintheactivationofthedirectuseofairundermildconditionsismore1enzymes.Manyoxidantsareavailabletoperformthisdesirable,notmanyexampleshavebeenreported,2keytransformation.Unfortunatelyoneorm

6、oreequiv-insteadmostofthemarebasedonhomogeneouscata-alents,oftenhazardousortoxicoxidizingagents,arelysts.12Thus,catalyticsystemsthatusedioxygenfromusuallyrequired.Otherwiseoveroxidationofsulfidestheairassecondaryoxidantaregreatlysoughtafter.resultinginsulfoneformationandundesiredreactio

7、nsOntheotherhand,clay-supportedmetallicnitratesofotherfunctionalgroupsarecommonproblems,par-havebeenwidelyusedasreagentsinorganicsynthesis,ticularlywhenpreparingbiologicallyrelevantsulfox-13particularlyinthefieldofoxidationandnitration.ides.FromaneconomicalandenvironmentalThereactivit

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