N-(2-chloro-2-propenyl)-2-bromoaniline | 133932-65-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-chloro-2-propenyl)-2-bromoaniline
• 英文别名: 2-bromo-N-(2-chloroprop-2-enyl)aniline
• CAS: 133932-65-7
• 化学式: C₉H₉BrClN
• mdl: MFCD12797685
• 分子量: 246.534
• InChiKey: SYOJJHDMEIQCBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-chloro-2-propenyl)-2-bromoaniline 在 (Ph₃P)4NiCl₂ 作用下， 以 二甲基亚砜 为溶剂， 以37 mg的产率得到3-甲基吲哚
  参考文献：
  名称：

  Electrocatalytic coupling of aryl halides with (1,2-bis(di-2-propylphosphino)benzene)nickel(0)

  摘要：

  Dibromo- and dichloro(1,2-bis(di-2-propylphosphino)benzene)nickel(II) is compared with tetrakis(triphenylphosphino)nickel(II) as an electrocatalyst for the reductive coupling of aryl halides. In many of the reactions examined, dehalogenation of the substrate predominated over coupling; however, preparative yields of biphenyls as high as 96% can be obtained with aryl chlorides and 2 mol % of the title catalyst in polar, coordinating solvents. Experimental factors governing the efficiency of these reactions are discussed, and possible mechanisms for coupling and catalyst deactivation are considered. Much better selectivity for aryl chlorides is attained in electroreductive couplings catalyzed by the title compound, whereas electrocatalysis with (Ph3P)4NiCl2 allows for selective intra- and intermolecular coupling at aryl bromide and vinyl chloride sites. Modest yields of cyclization products can be attained with either electrocatalyst in the presence of appropriately functionalized aryl or vinyl halides.

  DOI：

  10.1021/jo00010a014
• 作为产物：
  描述：

  2,3-二氯丙烯 、 2-溴苯胺 在 potassium carbonate 作用下， 反应 12.0h， 以20%的产率得到N-(2-chloro-2-propenyl)-2-bromoaniline
  参考文献：
  名称：

  Electrocatalytic coupling of aryl halides with (1,2-bis(di-2-propylphosphino)benzene)nickel(0)

  摘要：

  Dibromo- and dichloro(1,2-bis(di-2-propylphosphino)benzene)nickel(II) is compared with tetrakis(triphenylphosphino)nickel(II) as an electrocatalyst for the reductive coupling of aryl halides. In many of the reactions examined, dehalogenation of the substrate predominated over coupling; however, preparative yields of biphenyls as high as 96% can be obtained with aryl chlorides and 2 mol % of the title catalyst in polar, coordinating solvents. Experimental factors governing the efficiency of these reactions are discussed, and possible mechanisms for coupling and catalyst deactivation are considered. Much better selectivity for aryl chlorides is attained in electroreductive couplings catalyzed by the title compound, whereas electrocatalysis with (Ph3P)4NiCl2 allows for selective intra- and intermolecular coupling at aryl bromide and vinyl chloride sites. Modest yields of cyclization products can be attained with either electrocatalyst in the presence of appropriately functionalized aryl or vinyl halides.

  DOI：

  10.1021/jo00010a014

文献信息

• FOX, MARYE ANNE;CHANDLER, DANIEL A.;LEE, CHANGJIN, J. ORG. CHEM., 56,(1991) N0, C. 3246-3255
  作者：FOX, MARYE ANNE、CHANDLER, DANIEL A.、LEE, CHANGJIN

  DOI：——

  日期：——
• Electrocatalytic coupling of aryl halides with (1,2-bis(di-2-propylphosphino)benzene)nickel(0)
  作者：Marye Anne Fox、Daniel A. Chandler、Changjin Lee

  DOI：10.1021/jo00010a014

  日期：1991.5

  Dibromo- and dichloro(1,2-bis(di-2-propylphosphino)benzene)nickel(II) is compared with tetrakis(triphenylphosphino)nickel(II) as an electrocatalyst for the reductive coupling of aryl halides. In many of the reactions examined, dehalogenation of the substrate predominated over coupling; however, preparative yields of biphenyls as high as 96% can be obtained with aryl chlorides and 2 mol % of the title catalyst in polar, coordinating solvents. Experimental factors governing the efficiency of these reactions are discussed, and possible mechanisms for coupling and catalyst deactivation are considered. Much better selectivity for aryl chlorides is attained in electroreductive couplings catalyzed by the title compound, whereas electrocatalysis with (Ph3P)4NiCl2 allows for selective intra- and intermolecular coupling at aryl bromide and vinyl chloride sites. Modest yields of cyclization products can be attained with either electrocatalyst in the presence of appropriately functionalized aryl or vinyl halides.