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Ganiek, Maximilian A.; Becker, Matthias R.; Ketels, Marthe; Knochel, Paul (2016): Continuous Flow Magnesiation or Zincation of Acrylonitriles, Acrylates, and Nitroolefins. Application to the Synthesis of Butenolides. In: Organic Letters, Vol. 18, No. 4: pp. 828-831
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Scalable continuous flow procedures are reported for the metalation and downstream functionalization of beta-substituted acrylates. The flow conditions allow the metalation Of acrylonitriles, acrylates, and nitroolefins at 0.25-2.50 mmol/min conversion rates. Magnesiations can be performed with short residence times (1-20 min) and near-ambient temperature using TMPMgCl center dot LiCl. Further, high temperature zincation (<= 90 degrees C) using TMPZnCl.LiCl is possible. This method allows a simple entry to 2(5H)-furanones by flow generation of magnesiated acrylates and a subsequent reaction with aldehydes.