title: Palladium-catalyzed nitromethylation of aryl halides: an orthogonal formylation equivalent.
abstract: An efficient cross-coupling reaction of aryl halides and nitromethane was developed with the use of parallel microscale experimentation. The arylnitromethane products 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 that is compatible with many functional groups.
authors: Penn Merck High Throughput Experimentation Laboratory, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.
authors: Ryan R
authors: RR
authors: Walvoord
authors: Simon
authors: S
authors: Berritt
authors: Marisa C
authors: MC
authors: Kozlowski
mesh_terms: D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009595:Nitroparaffins / Q000737:chemistry*; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*
chemical_list: D006846:Hydrocarbons, Halogenated; D009595:Nitroparaffins; D010091:Oximes; D010165:Palladium; D008697:Methane; C008640:nitromethane