By Stacey L. McDonald
This thesis reviews the newest advancements within the direct amination of varied C−H bonds utilizing an H−Zn exchange/electrophilic amination method. McDonald and colleagues display this method of be a swift and robust procedure for having access to quite a few functionalized amines.
The fabric defined during this publication indicates how McDonald accomplished C−H zincation utilizing powerful, 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 concept for scientists coming into the sphere and scholars starting their PhD in a comparable sector.
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Additional info for Copper-Catalyzed Electrophilic Amination of sp2 and sp3 C−H Bonds
2 Initial Amination Studies Using the Reformatsky Reagent The Reformatsky enolate was ﬁrst reported by Sergey Reformatsky in the late 1800 s for condensation with aldehydes and ketones to give b-hydroxy esters [88, 89]. 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.
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. J Am Chem Soc 128(21):6790–6791 31. John A, Nicholas KM (2011) Copper-catalyzed amidation of 2-phenylpyridine with oxygen as the terminal oxidant. J Org Chem 76(10):4158–4162 32. Shuai Q, Deng G, Chua Z, Bohle DS, Li C-J (2010) Copper-catalyzed highly regioselective oxidative C–H bond amidation of 2-arylpyridine derivatives and 1-methylindoles.
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.