Continuous flow magnesiation or zincation of acrylonitriles, acrylates, and nitroolefins. Application to the synthesis of butenolides

• Maximilian A. Ganiek
• Matthias R. Becker
• Marthe Ketels
• Paul Knochel ^*

• Department of Chemistry, Ludwig-Maximilians-Universität, Butenandtstr. 5-13, 81377 Munich, Germany

Scalable continuous flow procedures are reported for the metalation and downstream functionalization of β-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·LiCl. Further, high temperature zincation (≤90 °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.

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