Continuous Flow Magnesiation or Zincation of Acrylonitriles, Acrylates, and Nitroolefins. Application to the Synthesis of Butenolides

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• 作者：Maximilian A. Ganiek ; Matthias R. Becker ; Marthe Ketels ; Paul Knochel
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：February 19, 2016
• 年：2016
• 卷：18
• 期：4
• 页码：828-831
• 全文大小：403K
• ISSN：1523-7052

文摘

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.