N,N-diethyl-4'-(trifluoromethyl)[1,1'-biphenyl]-4-carboxamide | 1620461-87-1

• 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: N,N-diethyl-4'-(trifluoromethyl)[1,1'-biphenyl]-4-carboxamide
• 英文别名: N,N-diethyl-4'-(trifluoromethyl)biphenyl-4-carboxamide
• CAS: 1620461-87-1
• 化学式: C₁₈H₁₈F₃NO
• 分子量: 321.342
• InChiKey: IJWLCYDOJXJHAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4-三氟甲基苯基溴化镁 在 C₃₈H₃₄Br₂N₄Ni₂P₂ 、 lithium chloride 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 12.0h， 生成 N,N-diethyl-4'-(trifluoromethyl)[1,1'-biphenyl]-4-carboxamide
  参考文献：
  名称：

  Mono- and Dinuclear Pincer Nickel Catalyzed Activation and Transformation of C–Cl, C–N, and C–O Bonds

  摘要：

  Condensation of 2-NH2C6H4P(Et)Ph (2) with pyrrole-2-carboxaldehyde generated 2-(C4H4N-2'-CH-N)C6H4P(Et)Ph (3). Treatment of 3 with NaH and followed by (DME)NiX2 (X = Cl, Br) afforded mononuclear pincer nickel complexes [Ni{2-(C4H3N-2'-CH-N)C6H4P(Et)Ph}X] (4a, X = Cl; 4b, X = Br). Reaction of [2-NH2C6H4P(Ph)](2)(CH2)(n) (5a, n = 3; 5b, n = 4) with pyrrole-2-carboxaldehyde or 5-tert-butyl-1H-pyrrole-2-carbaldehyde formed [2-(C4H4N-2'-CH-N)C6H4P(Ph)](2)(CH2)(n) (6a, n = 3; 6b, n = 4) and [2-(5'-tBuC(4)H(3)N-2'-CH-N)C6H4P(Ph)](2)(CH2)(4) (6c). Respective treatment of 6ac with NaH followed by (DME)NiX2 (X = Cl, Br) gave the dinuclear nickel complexes [Ni{2-(5'-RC4H2N-2'-CH-N)C6H4P(Ph)}X](2)(CH2)(n) (7a, R = H, X = Cl, n = 3; 7b, R = H, X = Cl, n = 4; 7c, R = H, X = Br, n = 4; 7d, R = tBu, X = Cl, n = 4). Catalysis of the complexes for the activation and transformation of CCl, CN, and CO bonds was evaluated. Complex 7c exhibited excellent catalytic activity in the cross-coupling of aryl chlorides or aryltrimethylammonium iodides with arylzinc reagents as well as of aryl sulfamates with aryl Grignard reagents. The dinuclear nickel complexes 7bd showed higher catalytic activity than the mononuclear complexes in each type of reaction.

  DOI：

  10.1021/om500452c

文献信息

• P,N,N-Pincer nickel-catalyzed cross-coupling of aryl fluorides and chlorides
  作者：Dan Wu、Zhong-Xia Wang

  DOI：10.1039/c4ob01041h

  日期：——

  were synthesized and their catalysis toward the Kumada or Negishi cross-coupling reaction of aryl fluorides and chlorides was evaluated. Complex 3a effectively catalyzes the cross-coupling of (hetero)aryl fluorides with aryl Grignard reagents at room temperature. Complex 3a also catalyzes the cross-coupling of (hetero)aryl chlorides and arylzinc reagents at 80 °C with low catalyst loadings and good

  P，N，N-镍镍配合物[Ni（Cl）N（2-R 2 PC 6 H 4）（2'-Me 2 NC 6 H 4）}]（R = Ph，3a ; R = Pr i，合成了3b； R ＝ Cy，3c），并评估了它们对芳基氟化物和氯化物的Kumada或Negishi交叉偶联反应的催化作用。在室温下，配合物3a有效催化（杂）芳基氟化物与芳基格氏试剂的交叉偶联。复杂3a 它还在低催化剂负载和良好的官能团相容性下，于80°C催化（杂）芳基氯和芳基锌试剂的交叉偶联。