title: Minimizing the amount of nitromethane in palladium-catalyzed cross-coupling with aryl halides.
abstract: A method for the formation of arylnitromethanes is described that employs readily available aryl halides or triflates and small amounts of nitromethane in a dioxane solvent, thereby reducing the hazards associated with this reagent. Specifically, 2-10 equiv (1-5% v/v) of nitromethane can be employed in comparison to prior work that used nitromethane as solvent (185 equiv). The present transformation provides high yields at relatively low temperatures and tolerates an array of functionality, including heterocycles and substantial steric encumbrance.
authors.affiliation: Penn Merck High Throughput Experimentation Laboratory, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: Ryan R
authors.initials: RR
authors.lastname: Walvoord
authors.forename: Marisa C
authors.initials: MC
authors.lastname: Kozlowski
mesh_terms: D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009595:Nitroparaffins / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006846:Hydrocarbons, Halogenated; D009595:Nitroparaffins; D010165:Palladium; D008697:Methane; C008640:nitromethane
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