2-bromo-N-tosyl-N-(2-methylallyl)aniline | 1191913-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-N-tosyl-N-(2-methylallyl)aniline
• 英文别名: N-(2-bromophenyl)-4-methyl-N-(2-methylprop-2-enyl)benzenesulfonamide
• CAS: 1191913-83-3
• 化学式: C₁₇H₁₈BrNO₂S
• 分子量: 380.305
• InChiKey: MLPZSYIOTIJEAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-N-tosyl-N-(2-methylallyl)aniline 在 Pd(Q-Phos)2 、 potassium iodide 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以91%的产率得到3-(iodomethyl)-3-methyl-1-tosylindoline
  参考文献：
  名称：

  Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes

  摘要：

  Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.

  DOI：

  10.1021/ja206099t
• 作为产物：
  描述：

  2-溴苯胺 在 potassium carbonate 、 三乙胺 、 potassium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 2-bromo-N-tosyl-N-(2-methylallyl)aniline
  参考文献：
  名称：

  EMM 促进的 Pd 催化固态分子内 Heck 型环化/硼化和 Suzuki 偶联：获得功能化二氢吲哚

  摘要：

  报道了 EMM（电磁磨）促进的 Pd 催化固态分子内 Heck 型环化/硼化和 Suzuki 偶联。与之前通过交叉偶联反应构建一个化学键的机械化学相比，该策略实现了级联转变以及多个化学键的形成。这种转化不需要有机溶剂或额外的加热，并且表现出良好的底物范围和高官能团耐受性。

  DOI：

  10.1021/acs.joc.3c02842

文献信息

• Domino Palladium-Catalyzed Heck-Intermolecular Direct Arylation Reactions
  作者：Olivier René、David Lapointe、Keith Fagnou

  DOI：10.1021/ol901799p

  日期：2009.10.15

  A domino palladium-catalyzed Heck-intermolecular direct arylation reaction has been developed, giving access to a variety of dihydrobenzofurans, indolines, and oxindoles. A variety of sulfur-containing heterocycles such as thiazoles, thiophenes, and benzothiophene can be employed as the direct arylation coupling partner in yields up to 99%.

  已经开发出多米诺骨牌钯催化的Heck分子间直接芳基化反应，使人们可以使用各种二氢苯并呋喃，二氢吲哚和羟吲哚。各种含硫杂环，如噻唑，噻吩和苯并噻吩可用作直接芳基化偶联伙伴，产率高达99％。
• Palladium-Catalyzed Domino Heck-Cyanation Cascade to 3-Cyanomethyl 2,3-Dihydrobenzofuran and 2,3-Dihydroindoles
  作者：Hyun-Seung Lee、Ko-Hoon Kim、Jin-Woo Lim、Jae-Nyoung Kim

  DOI：10.5012/bkcs.2011.32.3.1083

  日期：2011.3.20
• Palladium-Catalyzed Carbohalogenation: Bromide to Iodide Exchange and Domino Processes
  作者：Stephen G. Newman、Jennifer K. Howell、Norman Nicolaus、Mark Lautens

  DOI：10.1021/ja206099t

  日期：2011.9.28

  Aryl bromides have been used to prepare a variety of nitrogen- and oxygen-containing heterocycles featuring new carbon-carbon and carbon-iodine bonds. This palladium-catalyzed carbohalogenation requires potassium iodide for the reaction to proceed in high yields. Additionally, the first examples of domino carbohalogenation reactions have been demonstrated using both aryl iodide and aryl bromide starting materials. Complex products with multiple rings and stereogenic centers are generated in excellent yields with moderate to excellent diastereoselectivities.
• 10.1021/acs.joc.3c02842
  作者：Jia, Yuwei、Wang, Hui、Guo, Jintao、Zhang, Feng、Zhang, Lizhi、Li, Xinjin、Zhao, Yan、Bao, Xingliang、Liu, Qing、Li, Xiaowei、Liu, Hui

  DOI：10.1021/acs.joc.3c02842

  日期：——

  EMM (electromagnetic mill)-promoted Pd-catalyzed solid state intramolecular Heck-type cyclization/boronation and Suzuki couplings are reported. Compared to previous mechanochemistry that constructed one chemical bond through a cross-coupling reaction, this strategy realizes cascade transformation along with multiple chemical bond formation. This conversion does not require organic solvents or additional

  报道了 EMM（电磁磨）促进的 Pd 催化固态分子内 Heck 型环化/硼化和 Suzuki 偶联。与之前通过交叉偶联反应构建一个化学键的机械化学相比，该策略实现了级联转变以及多个化学键的形成。这种转化不需要有机溶剂或额外的加热，并且表现出良好的底物范围和高官能团耐受性。