4-(pyridin-2-yl)-[1,1'-biphenyl]-3-carbonitrile | 1235409-61-6

• 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: 4-(pyridin-2-yl)-[1,1'-biphenyl]-3-carbonitrile
• 英文别名: 5-phenyl-2-(pyridin-2-yl)benzonitrile；5-Phenyl-2-pyridin-2-ylbenzonitrile
• CAS: 1235409-61-6
• 化学式: C₁₈H₁₂N₂
• 分子量: 256.307
• InChiKey: USZACNRXFFWMPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-phenylphenyl)pyridine 、 N-(tert-butyl)benzimidoyl cyanide 在 palladium diacetate 、 copper(II) trifluoroacetate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以63%的产率得到4-(pyridin-2-yl)-[1,1'-biphenyl]-3-carbonitrile
  参考文献：
  名称：

  α-Iminonitrile: a new cyanating agent for the palladium catalyzed C–H cyanation of arenes

  摘要：

  一种高效的钯催化芳烃C-H氰化反应已经开发出来，使用α-亚胺腈作为新的氰化试剂。

  DOI：

  10.1039/c6ra14512d

文献信息

• Copper-catalyzed cyanation of arenes using benzyl nitrile as a cyanide anion surrogate
  作者：Jisong Jin、Qiaodong Wen、Ping Lu、Yanguang Wang

  DOI：10.1039/c2cc35046g

  日期：——

  The copper-catalyzed cyanation of arenes using benzyl nitrile as a cyanide anion surrogate furnishes aromatic nitriles in moderate to good yields. The cascade process involves a copper-catalyzed aerobic C-H oxidation, a retro-cyanohydrination, and a copper-catalyzed aerobic oxidative C-H functionalization.

  使用苄基腈作为氰化物阴离子替代物进行的铜催化的芳烃氰化，可提供中等至良好收率的芳族腈。级联过程涉及铜催化的好氧CH氧化，逆向氰化和铜催化的好氧氧化CH官能化。
• A Pd(<scp>ii</scp>)/Mg–La mixed oxide catalyst for cyanation of aryl C–H bonds and tandem Suzuki–cyanation reactions
  作者：Ramineni Kishore、Jagjit Yadav、Boosa Venu、Akula Venugopal、M. Lakshmi Kantam

  DOI：10.1039/c5nj00585j

  日期：——

  A palladium(II)/magnesium–lanthanum mixed oxide (Pd(II)/Mg–La) catalyst is a reusable catalyst for cyanation of aromatic C–H bonds by using the combination of NH4HCO3 and DMSO as the ‘‘CN’’ source. Moderate to good yields of aromatic nitriles were obtained. An excellent regioselectivity was achieved using the present protocol. A tandem process involving Suzuki coupling followed by a cyanation reaction

  钯（II）/镁-镧混合氧化物（Pd（II）/ Mg-La）催化剂是可重复使用的催化剂，通过使用NH 4 HCO 3和DMSO的组合将芳族CH键氰化'' 资源。获得了中等至良好产率的芳族腈。使用本方案实现了极好的区域选择性。还使用非均相（Pd（II）/ Mg-La）催化剂开发了涉及Suzuki偶联并随后发生氰化反应的串联过程。该级联过程导致由简单的2-卤代吡啶形成芳族腈。通过离心回收催化剂，并以连续的三个循环重复使用，具有几乎一致的活性和选择性。
• Cobalt-Catalyzed C–H Cyanation of (Hetero)arenes and 6-Arylpurines with <i>N</i>-Cyanosuccinimide as a New Cyanating Agent
  作者：Amit B. Pawar、Sukbok Chang

  DOI：10.1021/ol503680d

  日期：2015.2.6

  A cobalt-catalyzed C–H cyanation reaction of arenes has been developed using N-cyanosuccinimide as a new electrophilic cyanating agent. The reaction proceeds with high selectivity to afford monocyanated products with excellent functional group tolerance. Substrate scope was found to be broad enough to include a wide range of heterocycles including 6-arylpurines.

  使用N-氰基琥珀酰亚胺作为新型的亲电子氰化剂，已开发出钴催化芳烃的CH氰化反应。反应以高选择性进行，得到具有优异的官能团耐受性的单氰酸酯化产物。发现底物的范围足够宽，可以包括包括6-芳基嘌呤在内的各种杂环。
• Rhodium(<scp>iii</scp>)-catalyzed aromatic C–H cyanation with dimethylmalononitrile as a cyanating agent
  作者：He Li、Sheng Zhang、Xiaoqiang Yu、Xiujuan Feng、Yoshinori Yamamoto、Ming Bao

  DOI：10.1039/c8cc08930b

  日期：——

  A rhodium-catalyzed aromatic C–H bond direct cyanation with safe, bench-stable, and commercially available dimethylmalononitrile as the cyanating agent has been successfully developed by using copper oxide as a promotor. Pyridine, quinoline, pyrimidine and pyrazole were used as the directing group in this type of C–H bond direct cyanation reaction.

  通过使用氧化铜作为促进剂，成功开发出了铑催化的芳香族CH键直接氰化，安全，稳定和可商购的二甲基丙二腈作为氰化剂。吡啶，喹啉，嘧啶和吡唑被用作这种C–H键直接氰化反应的导向基团。
• C–H bond cyanation of arenes using N,N-dimethylformamide and NH₄HCO₃ as a CN source over a hydroxyapatite supported copper catalyst
  作者：Boosa Venu、Bilakanti Vishali、Gutta Naresh、Velisoju Vijay Kumar、Medak Sudhakar、Ramineni Kishore、Jorge Beltramini、Muxina Konarova、Akula Venugopal

  DOI：10.1039/c6cy01536k

  日期：——

  Copper dispersed on Ca₅(PO₄)₃OH has been identified as an excellent heterogeneous catalyst for the in situ generation of ‘CN’ from NH₄HCO₃ and N,N-dimethylformamide, in the C–H bond activation of 2-phenylpyridine.

  在Ca₅(PO₄)₃OH上分散的铜被确认为一种优秀的非均相催化剂，用于在2-苯基吡啶的C-H键活化中，通过NH₄HCO_{3和N,N-二甲基甲酰胺生成‘CN’。}