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Rh(III)-Catalyzed Synthesis of Multisubstituted Isoquinoline and Pyridine N-Oxides from Oximes and Diazo Compounds

Zhuangzhi Shi, Dennis C. Koester, Mélissa Boultadakis-Arapinis and Frank Glorius*

*Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany, Email: gloriusuni-muenster.de

Z. Shi, D. C. Koester, M. Boultadakis-Arapinis, F. Glorius, J. Am. Chem. Soc., 2013, 135, 12204-12205.

DOI: 10.1021/ja406338r (free Supporting Information)


Abstract

An intermolecular, Rh(III)-catalyzed cyclization of oximes and diazo compounds involving tandem C-H activation, cyclization, and condensation steps gives multisubstituted isoquinoline and pyridine N-oxides under mild conditions. The reaction obviates the need for oxidants, releases N2 and H2O as the byproducts, and displays a broad substituent scope.

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Key Words

Isoquinolines, Pyridines


ID: J48-Y2013