1352965-43-5Relevant articles and documents
Copper-catalyzed mild nitration of protected anilines
Hernando, Elier,Castillo, Rafael R.,Rodríguez, Nuria,G?mez Arrayás, Ram?n,Carretero, Juan C.
supporting information, p. 13854 - 13859 (2016/02/18)
A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.
PdII-catalyzed C-H olefination of N-(2-pyridyl)sulfonyl anilines and arylalkylamines
Garcia-Rubia, Alfonso,Urones, Beatriz,Gomez Arrayas, Ramon,Carretero, Juan C.
supporting information; experimental part, p. 10927 - 10931 (2012/01/04)
Flexible friend: The N-(2-pyridyl)sulfonyl group acts as a removable directing group in the PdII-catalyzed aryl C-H ortho alkenylation of N-alkyl aniline, benzylamine, and phenethylamine derivatives with electron-poor alkenes. The products were obtained in high yields (70-90 %) and with complete regiocontrol. The mild reductive N-sulfonyl removal enables the construction of a variety of nitrogen heterocycles. EWG=electron-withdrawing group.