Rh2(II)-Catalyzed Ring Expansion of Cyclobutanol-Substituted Aryl Azides To Access Medium-Sized N-Heterocycles
Journal of the American Chemical Society2017Vol. 139(14), pp. 5031–5034
Citations Over TimeTop 10% of 2017 papers
Abstract
A new reactivity pattern of Rh2(II)-N-arylnitrenes was discovered that facilitates the synthesis of medium-sized N-heterocycles from ortho-cyclobutanol-substituted aryl azides. The key ring-expansion step of the catalytic cycle is both chemoselective and stereospecific. Our mechanistic experiments implicate the formation of a rhodium N-arylnitrene catalytic intermediate and reveal that sp3 C-H bond amination of this electrophilic species is competitive with the ring-expansion process.
Related Papers
- → Atomically dispersed rhodium on a support: the influence of a metal precursor and a support(2014)14 cited
- → Factors determining rhodium solubilization efficiency in molten K2CO3–K2O–B2O3–Al2O3 medium(2023)2 cited
- → The effect of rhodium precursor on Rh/Al2O3 catalysts(1982)54 cited
- → ChemInform Abstract: BASIC METALS. XI. CATIONIC (CYCLOPENTADIENYL)RHODIUM COMPLEXES CONTAINING RHODIUM‐HYDROGEN, RHODIUM‐CARBON, RHODIUM‐GERMANIUM, RHODIUM‐TIN, AND RHODIUM‐HALOGEN BONDS(1979)
- Progress in Rhodium Determination Method for Rhodium-containing Materials(2014)