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Minimizing the Amount of Nitromethane in Palladium-Catalyzed Cross-Coupling with Aryl Halides

Ryan R. Walvoord and Marisa C. Kozlowski*

*Penn Merck High Throughput Experimentation Laboratory, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States, Email: marisasas.upenn.edu

R. R. Walvoord, M. C. Kozlowski, J. Org. Chem., 2013, 78, 8859-8864.

DOI: 10.1021/jo401249y (free Supporting Information)



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Abstract

In a Pd-catalyzed formation of arylnitromethanes from readily available aryl halides or triflates, 2-10 equiv of nitromethane in dioxane as solvent can be employed in comparison to prior work that used nitromethane as solvent (185 equiv). The present transformation reduces the hazards associated with MeNO2, provides high yields at relatively low temperatures, and tolerates an array of functionality.

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Palladium-Catalyzed Nitromethylation of Aryl Halides: An Orthogonal Formylation Equivalent

R. R. Walvoord, S. Berritt, M. C. Kozlowski, Org. Lett., 2012, 14, 4086-4089.


Key Words

α-arylation, nitro compounds


ID: J42-Y2013