19015-37-3Relevant articles and documents
Palladium and Nickel Catalyzed Suzuki Cross-Coupling with Alkyl Fluorides
Balaraman, Kaluvu,Wolf, Christian
supporting information, p. 8994 - 8999 (2021/11/20)
Suzuki cross-coupling of benzylic and unactivated aliphatic fluorides with aryl- and alkenylboronic acids has been achieved via mechanistically distinct Pd and Ni catalyzed pathways that outperform competing protodeboronation, β-hydride elimination, and h
Chiral cyclometalated iridium complexes for asymmetric reduction reactions
Smith, Jennifer,Kacmaz, Aysecik,Wang, Chao,Villa-Marcos, Barbara,Xiao, Jianliang
supporting information, p. 279 - 284 (2021/01/18)
A series of chiral cyclometalated iridium complexes have been synthesised by cyclometalating chiral 2-aryl-oxazoline and imidazoline ligands with [Cp?IrCl2]2. These iridacycles were studied for asymmetric transfer hydrogenation reactions with formic acid as the hydrogen source and were found to display various activities and enantioselectivities, with the most effective ones affording up to 63% ee in the asymmetric reductive amination of ketones and 77% ee in the reduction of pyridinium ions. This journal is
Transition-Metal-Free Deconstructive Lactamization of Piperidines
Romero-Iba?ez, Julio,Cruz-Gregorio, Silvano,Sandoval-Lira, Jacinto,Hernández-Pérez, Julio M.,Quintero, Leticia,Sartillo-Piscil, Fernando
supporting information, p. 8867 - 8871 (2019/05/28)
One of the major challenges in organic synthesis is the activation or deconstructive functionalization of unreactive C(sp3)–C(sp3) bonds, which requires using transition or precious metal catalysts. We present here an alternative: the deconstructive lactamization of piperidines without using transition metal catalysts. To this end, we use 3-alkoxyamino-2-piperidones, which were prepared from piperidines through a dual C(sp3)–H oxidation, as transitory intermediates. Experimental and theoretical studies confirm that this unprecedented lactamization occurs in a tandem manner involving an oxidative deamination of 3-alkoxyamino-2-piperidones to 3-keto-2-piperidones, followed by a regioselective Baeyer–Villiger oxidation to give N-carboxyanhydride intermediates, which finally undergo a spontaneous and concerted decarboxylative intramolecular translactamization.