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Control over the formation of N-formylamides versus the formation of captodative alkenes from the reaction of arylacetic acids with isonitriles has been achieved. Low temperatures and high concentrations favor alkenes, and high temperatures and low concentrations favor N-formylamides.
Isonitriles react with low concentrations of carboxylic acids in toluene at 110°C to give N-formylamides in yields generally above 70%. These concentrations can be obtained either by syringe pump addition of a toluene solution of the acid, or by using a suspension of the acid if it has limited solubility in toluene at room temperature.
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