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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.

SUBMITTER: Walvoord RR 

PROVIDER: S-EPMC3778657 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Minimizing the amount of nitromethane in palladium-catalyzed cross-coupling with aryl halides.

Walvoord Ryan R RR   Kozlowski Marisa C MC  

The Journal of organic chemistry 20130813 17


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, incl  ...[more]

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