2-Phenyl-5,6-methylendioxyphthalimidin | 4770-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-Phenyl-5,6-methylendioxyphthalimidin
• 英文别名: 6-phenyl-6,7-dihydro-[1,3]dioxolo[4,5-f]isoindol-5-one
• CAS: 4770-82-5
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: HLFUNISKMFHVTL-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  二氧化碳 、 N-((6-bromobenzo[d][1,3]dioxol-5-yl)methyl)aniline 在 aluminum (III) chloride 、 1,2-双[(2R,5R)-2,5-二乙基磷杂环戊烷基]苯(1,5-环辛二烯)铑(I)四氟硼酸盐 、 N,N-二异丙基乙胺 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到2-Phenyl-5,6-methylendioxyphthalimidin
  参考文献：
  名称：

  Direct Access to Benzolactams and Benzolactones via Nickel Catalyzed Carbonylation with CO2

  摘要：

  A new nickel catalyzed cross‐electrophile coupling for accessing γ‐lactams (isoindolinones) as well as γ‐lactones (isobenzofuranones) via carbonylation with CO2 is documented. The protocol exploits the synergistic role of redox‐active Ni(II) complexes and AlCl3 as a CO2 activator/oxygen scavenger, leading to the formation of a wide range of cyclic amides and esters (28 examples) in good to high yields (up to 87%). A dedicated computational investigation revealed the multiple roles played by AlCl3. In particular, the simultaneous transient protection of the pendant amino group of the starting reagents and the formation of the electrophilically activated CO2‐AlCl3 adduct are shown to concur in paving the way for an energetically favorable mechanistic pathway.

  DOI：

  10.1002/chem.202401658