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Rh(III)-catalyzed synthesis of multisubstituted isoquinoline and pyridine N-oxides from oximes and diazo compounds.

Journal of the American Chemical Society (2013-07-31)
Zhuangzhi Shi, Dennis C Koester, Mélissa Boultadakis-Arapinis, Frank Glorius
RESUMEN

Multisubstituted isoquinoline and pyridine N-oxides have been prepared by Rh(III)-catalyzed cyclization of oximes and diazo compounds via aryl and vinylic C-H activation. This intermolecular annulation involving tandem C-H activation, cyclization, and condensation steps proceeds under mild conditions, obviates the need for oxidants, releases N2 and H2O as the byproducts, and displays a broad substituent scope.

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Sigma-Aldrich
Dimethyl (1-diazo-2-oxopropyl)phosphonate solution, ~10% in acetonitrile (H-NMR), ≥96% (HPLC)