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Download Copper-Catalyzed Electrophilic Amination of sp2 and sp3 C−H by Stacey L. McDonald PDF

By Stacey L. McDonald

This thesis studies the newest advancements within the direct amination of varied C−H bonds utilizing an H−Zn exchange/electrophilic amination procedure. McDonald and colleagues exhibit this method of be a speedy and strong technique for getting access to various functionalized amines.

The fabric defined during this booklet indicates how McDonald completed C−H zincation utilizing robust, non-nucleophilic zinc bases and next electrophilic amination of the corresponding zinc carbanions with copper as a catalyst and O-benzoylhydroxylamines because the electrophilic nitrogen resource.

McDonald’s findings are of relevance to medicinal chemistry, drug discovery and fabrics technology. Her thesis is a resource of suggestion for scientists getting into the sector and scholars starting their PhD in a comparable zone.

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Extra info for Copper-Catalyzed Electrophilic Amination of sp2 and sp3 C−H Bonds

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9) and is less nucleophilic than lithium enolates or Grignard reagents. 3 mmol scale b Time required for the complete consumption of 3 c Yields determined by 1H NMR spectroscopy with CH2Br2 as a quantitative internal standard d Reaction with pre-formed catalyst [(iPr)CuCl] gave 13 % amination With this we chose to start the development of our a-amination method using Reformatsky enolate 2. 1). Using ICyÁBF4 as the ligand, a-amino ester 4 was observed in 13 % (entry 1). Minor amination was observed using IMesÁHCl and iPr (entries 3 and 4), while no amination was observed for SIMesÁHBF4 or iPrÁHCl (entries 2 and 5).

J Org Chem 76(19):7938–7944 28. Wertz S, Kodama S, Studer A (2011) Amination of benzoxazoles and 1,3,4-oxadiazoles using 2,2,6,6-tetramethylpiperidine-N-oxoammonium tetrafluoroborate as an organic oxidant. Angew Chem Int Ed 50(48):11511–11515 References 19 29. Yotphan S, Beukeaw D, Reutrakul V (2013) A convenient one-pot synthesis of N-substituted 2-aminoazole derivatives. Synthesis 45(7):936–942 30. Chen X, Hao X-S, Goodhue CE, Yu J-Q (2006) Cu(II)-catalyzed functionalizations of aryl C −H bonds using O2 as an oxidant.

However the substrate scope is limited due to the strongly basic reaction conditions as well as the competing chlorination reaction. 5) [41]. Their mild reaction conditions readily afforded the corresponding a-amino esters in good to moderate yields. A variety of N-chloramines, cyclic and acyclic, worked well; however silyl ketene acetals were limited to benzyl methyl esters. 6) [43]. Various silyl ketene acetals underwent amination with O-benzoyl-N,N-dibenzylhydroxylamine to give the corresponding a-amino esters.

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