N-[2-(4-methoxyphenyl)ethyl]naphthalene-2-sulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[2-(4-methoxyphenyl)ethyl]naphthalene-2-sulfonamide
• 化学式: C₁₉H₁₉NO₃S
• 分子量: 341.4
• InChiKey: GBDOIZVPUDDGME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-naphthalenesulphonyl azide 、 4-甲氧基苯乙烯 在 二氢吡啶 、 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene 、 4-甲苯硫酚 作用下， 以 1,2-二氯乙烷 为溶剂， 以73 %的产率得到N-[2-(4-methoxyphenyl)ethyl]naphthalene-2-sulfonamide
  参考文献：
  名称：

  Organo‐Photocatalytic Anti‐Markovnikov Hydroamidation of Alkenes with Sulfonyl Azides: A Combined Experimental and Computational Study

  摘要：

  The construction of C(sp3)−N bonds via direct N‐centered radical addition with olefins under benign conditions is a desirable but challenging strategy. Herein, we describe an organo‐photocatalytic approach to achieve anti‐Markovnikov alkene hydroamidation with sulfonyl azides in a highly efficient manner under transition‐metal‐free and mild conditions. A broad range of substrates, including both activated and unactivated alkenes, are suitable for this protocol, providing a convenient and practical method to construct sulfonylamide derivatives. A synergistic experimental and computational mechanistic study suggests that the additive, Hantzsch ester (HE), might undergo a triplet‐triplet energy transfer manner to achieve photosensitization by the organo‐photocatalyst under visible light irradiation. Next, the resulted triplet excited state 3HE* could lead to a homolytic cleavage of C4−H bond, which triggers a straightforward H‐atom transfer (HAT) style in converting sulfonyl azide to the corresponding key amidyl radical. Subsequently, radical addition of the amidyl radical to alkenes followed by HAT from p‐toluenethiol could proceed to afford the desired anti‐Markovnikov hydroamidation product. It is worth noting that mechanistic pathway bifurcation could be possible for this reaction. A feasible radical chain propagation mechanistic pathway is also proposed to rationalize the high efficiency of this reaction.

  DOI：

  10.1002/anie.202406069