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

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

DOI: 10.1021/ol301713j (free Supporting Information)


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Abstract

An efficient cross-coupling reaction of aryl halides and nitromethane gives arylnitromethane products, that are precursors for numerous useful synthetic products. An efficient method for their direct conversion to the corresponding oximes and aldehydes in a one-pot operation has been discovered. The process exploits inexpensive nitromethane as a carbonyl equivalent, providing a mild and convenient formylation method.

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

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

Efficient Palladium-Catalyzed Cross-Coupling of Highly Acidic Substrates, Nitroacetates

A. E. Metz, S. Berritt, S. D. Dreher, M. C. Kozlowski, Org. Lett., 2012, 14, 760-763.


Key Words

Nitro Compounds, α-Arylation


ID: J54-Y2012-2520