487-19-4Relevant articles and documents
An improved synthesis of β-Nicotyrine from the dehydrogenation of nicotine: Comparison of conventional and microwave-assisted reactions
Wei, Xiaochen,Crooks, Peter A.
, p. 3305 - 3315 (2003)
β-Nicotyrine, a minor tobacco alkaloid, can be rapidly prepared in good yield from the dehydrogenation of S-(-)-nicotine over MnO2 with microwave irradiation. This method is superior to dehydrogenation reactions that utilize S-(-)-nicotine and MnO2 in a variety of solvents under reflux.
C2-Selective silylation of pyridines by a rhodium-aluminum complex
Hara, Naofumi,Uemura, Nao,Nakao, Yoshiaki
supporting information, p. 5957 - 5960 (2021/06/18)
We have developed a C2-selective mono-silylation of a variety of pyridines using a Rh-Al complex. Both the site- and mono-selectivity are controlledviathe pyridine coordination to the Lewis-acidic Al center prior to the activation of the pyridine C(2)-H bond at the proximal Rh center. A reaction mechanism is proposed based on several mechanistic studies, including the isolation of a (2-pyridyl)silylrhodium intermediate.
A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry
Constantin, Timothée,Juliá, Fabio,Leonori, Daniele,Sheikh, Nadeem S.
, p. 12822 - 12828 (2020/12/29)
The generation of aryl radicals from the corresponding halides by redox chemistry is generally considered a difficult task due to their highly negative reduction potentials. Here we demonstrate that α-aminoalkyl radicals can be used as both initiators and chain-carriers for the radical coupling of aryl halides with pyrrole derivatives, a transformation often employed to evaluate new highly reducing photocatalysts. This mode of reactivity obviates for the use of strong reducing species and was also competent in the formation of sp2 C-P bonds. Mechanistic studies have delineated some of the key features operating that trigger aryl radical generation and also propagate the chain process.