8-(4-butylphenyl)-4-methyl-2,6-dioxohexahydro-8l4-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium | 1422263-65-7

• 英文名称: 8-(4-butylphenyl)-4-methyl-2,6-dioxohexahydro-8l4-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium
• CAS: 1422263-65-7
• 化学式: C₁₅H₂₀BNO₄
• 分子量: 289.139
• InChiKey: UDPIDLRXZYFQDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
  None
• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  8-(4-butylphenyl)-4-methyl-2,6-dioxohexahydro-8l4-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium 在 (tBuCN)2Cu*OTf 、 silver fluoride 、 N-fluorobis<(trifluoromethyl)sulfonyl>imide 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以23%的产率得到丁苯
  参考文献：
  名称：

  Copper-Mediated Fluorination of Arylboronate Esters. Identification of a Copper(III) Fluoride Complex

  摘要：

  A method for the direct conversion of arylboronate esters to aryl fluorides under mild conditions with readily available reagents is reported. Tandem reactions have also been developed for the fluorination of arenes and aryl bromides through arylboronate ester intermediates. Mechanistic studies suggest that this fluorination reaction occurs through facile oxidation of Cu(I) to Cu(III), followed by rate-limiting transmetalation of a bound arylboronate to Cu(III). Fast C-F reductive elimination is proposed to occur from an aryl- copper(III)-fluoride complex. Cu(III) intermediates have been generated independently and identified by NMR spectroscopy and ESI-MS.

  DOI：

  10.1021/ja310909q