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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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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R. R. Walvoord, M. C. Kozlowski, J. Org. Chem., 2013, 78, 8859-8864.
A. E. Metz, S. Berritt, S. D. Dreher, M. C. Kozlowski, Org. Lett., 2012, 14, 760-763.