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Application Of Phosphine Ligand Adducts Of Cyclopalladated Ferrocenylimine To Suzuki Reaction Containing Organotrifluoroborates

Posted on:2011-05-10Degree:MasterType:Thesis
Country:ChinaCandidate:H M CuiFull Text:PDF
GTID:2121330332958697Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
In this thesis, the application of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos) adduct of cyclopalladated ferrocenylimine complexⅡf in Suzuki reaction was studied. The construction of benzylic sulfonamides in the presence of N,N-dimethylα-trimethylsilylsulfonamide by the catalysts of various palladium sources was also studied.1. The application of the catalystⅡf in the aminomethylation of aryl and heteroaryl halides with potassium alkyltrifluoroborates was studied. It was found that potassium N,N-dialkylaminomethyltrifluoroborates could effectively couple with aryl and heteroaryl halides in the 10:1 THF/H2O mixture at 80℃in the presence of Cs2CO3 (3.0 equiv) as the base, giving the desired compounds in 14-87% yields. A variety of potassium alkyltrifluoroborates were also examined. (Scheme 1)2. The application of several kinds of Pd catalyst systems in the reaction of N, N-dimethyl a-trimethylsilylsulfonamide with bromobenzene was studied. Under optimized condition (catalyst:Pd2(dba)3'CHCl3; liand:Xphos; activators:Ag2O and 0.1 eq TBAF; under 70℃using DMF last 12h), the yield was 22% which was detected by GC-MS.
Keywords/Search Tags:Cyclopalladated ferrocenylimines, aryl halides, Aminomethylation, potassium N,N-dialkylaminomethyltrifluoroborates, N,N-dimethylα-trimethylsilylsulfonamide, benzylic sulfonamides
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