137152-15-9Relevant academic research and scientific papers
A new generation of terminal copper nitrenes and their application in aromatic C-H amination reactions
Amarouch, Benedikt,G?bgen, Kai C.,Hoffmann, Alexander,Oster, Matthias,Sch?n, Florian,Steden, Dominik,Thomas, Fabian
supporting information, p. 6444 - 6462 (2021/05/26)
Copper nitrene complexes are highly reactive species and are known as intermediates in the copper catalyzed C-H amination. In this study, three novel copper tosyl nitrene complexes were synthesized at low temperatures, stabilized with heteroscorpionate ligands of the bis(pyrazolyl)methane family. The copper nitrenes were obtained by the reaction of a copper(i) acetonitrile complex with SPhINTs in dichloromethane. We show that the ligand design has a major influence on the catalytic activity and the thermal stability of the copper nitrene complex. Not only the choice of the third N donor, but also the substituent in the 5-position of the pyrazolyl moiety, have an impact on the stability. Furthermore, the novel copper nitrene complexes were used for catalytic aziridination of styrenes and C-H amination reactions of aromatic and aliphatic substrates under mild reaction conditions. Even challenging substrates like benzene and cyclohexane were aminated with good yields. The copper nitrene complexes were characterized using UV/Vis spectroscopy, low temperature Evans NMR spectroscopy, density functional theory, domain-based local pair natural orbital coupled cluster calculations (DLPNO-CCSD(T)) and cryo-UHR mass spectrometry.
Catalyst-free aziridination and unexpected homologation of aziridines from imines
Branco, Paula Serio,Raje, Vivek Prabhakar,Dourado, Jorge,Gordo, Joana
experimental part, p. 2968 - 2974 (2010/09/06)
Aziridination and unpredicted homologation reaction of N-sulfonylimines were achieved easily with a very simple, rapid and mild procedure through the use of diazomethane without the presence of any catalyst. The method represents an attractive alternative
Methylene Transfer from Dimethyloxosulphonium Methylide to N-Arylsulphonylaziridines: Stereospecific Synthesis of N-Arylsulphonylazetidines
Nadir, Upender K.,Sharma, Ms. Raman L.,Koul, Veerinder K.
, p. 2015 - 2020 (2007/10/02)
Several 2-alkyl, 2-aryl-, 2-benzyl-, 2,3-dialkyl- and 2,3-diarylsulphonylazetidines have been prepared in fair to good isolated yields through reaction of N-arylsulphonylaziridines with dimethyloxosulphonium methylide.Fused azetidines, however, could not
