1.2.3.4-Tetrahydro-chinolin-2.2-d2 | 20668-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1.2.3.4-Tetrahydro-chinolin-2.2-d2
• 英文别名: 2,2-d2-Tetrahydrochinolin；2,2-dideuterio-1,2,3,4-tetrahydro-quinoline
• CAS: 20668-18-2
• 化学式: C₉H₁₁N
• 分子量: 135.177
• InChiKey: LBUJPTNKIBCYBY-RJSZUWSASA-N

反应信息

• 作为反应物：
  描述：

  1.2.3.4-Tetrahydro-chinolin-2.2-d2 在 三乙胺 、 lithium tert-butoxide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Photoinduced Electron Donor Acceptor Complex‐Enabled α‐C(sp3)−H Alkenylation of Amines

  摘要：

  Allylic amines are prevalent and vital structural components present in many bioactive compounds and natural products. Additionally, they serve as valuable intermediates and building blocks, with wide‐ranging applications in organic synthesis. However, direct α‐C(sp3)‐H alkenylation of feedstock amines, particularly for the preparation of α‐alkenylated cyclic amines, has posed a longstanding challenge. Herein, we present a general, mild, operationally simple, and transition‐metal‐free α‐alkenylation of various readily available amines with alkenylborate esters in excellent E/Z ‐ and diastereoselectivities. This method features good compatibility with water and oxygen, broad substrate scope, and excellent functional group tolerance, thereby enabling the late‐stage modification of various complex molecules. Mechanistic studies suggest that the formation of a photoactive electron donor‐acceptor complex between 2‐iodobenzamide and the tetraalkoxyborate anion, which subsequently undergoes photoinduced single electron transfer and intramolecular 1,5‐hydrogen atom transfer to generate the crucial α‐amino radicals, is the key to success of this chemistry.

  DOI：

  10.1002/anie.202409310