2-bromo-2-(2-thienyl)-1,1-difluoroethene | 769147-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-bromo-2-(2-thienyl)-1,1-difluoroethene
• 英文别名: 2-(2-bromo-1,1-difluoroethenyl)thiophene；2-(1-Bromo-2,2-difluoroethenyl)thiophene
• CAS: 769147-09-3
• 化学式: C₆H₃BrF₂S
• 分子量: 225.057
• InChiKey: OIGMYAVPQQTSAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-噻吩硼酸 、 2-bromo-2-(2-thienyl)-1,1-difluoroethene 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙醇 、 水 、 苯 为溶剂， 反应 28.0h， 以74%的产率得到2-(2-thienyl)-2-(3-thienyl)-1,1-difluoroethene
  参考文献：
  名称：

  New Efficient Approach to 2,2-Diaryl-1,1-difluoro-1-alkenes and 1,1-Difluoro-2-aryl-1,3-dienes via Suzuki Coupling of α-Halo-β,β-difluorostyrenes

  摘要：

  [Graphics]a-Halo-beta,beta-difluorostyrenes [ArCX = CF2; X = Br, I; Ar = aryl, heteroaryl; synthesized by the Pd(0)-catalyzed coupling reaction of the corresponding alpha-halo-beta,beta-difluoroethenylzinc reagents (CF2=CXZnCl, X = Br, I) with aryl iodides] were functionalized at the halogen site with arylboronic acids under Pd(0)-catalyzed Suzuki-Miyaura coupling reaction conditions to obtain 2,2-diaryl-1,1-difluoro-1-alkenes (ArAr'C=CF2, Ar' = aryl, heteroaryl) in 51-91% isolated yield. The corresponding reaction with alkenylboronic acids produced 1,1-difluoro-2-aryl-1,3-dienes in 53-80% isolated yield. Alternatively, 2,2-disubstituted-1,1-difluoro-1-alkenes were synthesized in moderate yield by a zinc-insertion reaction at the halogen site of the alpha-halo-beta,beta-difluorostyrenes, followed by Pd(0)-catalyzed cross-coupling of the zinc reagent with aryl or alkenyl iodides.

  DOI：

  10.1021/jo051842p
• 作为产物：
  描述：

  2-碘噻吩 、 一溴三氟乙烷 在 四(三苯基膦)钯 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 以64%的产率得到2-bromo-2-(2-thienyl)-1,1-difluoroethene
  参考文献：
  名称：

  溴difluorovinylzinc试剂（CF的有效室温制备2 CBrZnCl）和α溴-β的高产率一锅合成，β-difluorostyrenes

  摘要：

  THE1溴-2,2- difluorovinylzinc试剂的高收率室温制备[CF 2 CBrZnCl]（> 89％）中的溶液经由CF的原位金属化实现3 CH 2 Br或CF 2中的ZnCl的存在CHBr用LDA 2。钯催化此锌试剂与芳基碘化物的交叉偶联提供了α溴-β，β-trifluorostyrenes（ArCBrCF 2）在64-86％的分离产率，以基本上“一锅煮”过程。

  DOI：

  10.1016/j.jfluchem.2003.11.029

文献信息

• An efficient room temperature preparation of bromo difluorovinylzinc reagent (CF2CBrZnCl) and a high yield one-pot synthesis of α-bromo-β,β-difluorostyrenes
  作者：R. Anilkumar、Donald J. Burton

  DOI：10.1016/j.jfluchem.2003.11.029

  日期：2004.4

  A high yield room temperature preparation of the1-bromo-2,2-difluorovinylzinc reagent [CF2CBrZnCl] (>89%) was achieved via insitu metallation of CF3CH2Br or CF2CHBr with LDA in presence of ZnCl2. Palladium catalyzed cross-coupling of this zinc reagent with aryl iodides provides α-bromo-β,β-trifluorostyrenes (ArCBrCF2) in 64–86% isolated yields, in an essentially ‘one-pot’ procedure.

  THE1溴-2,2- difluorovinylzinc试剂的高收率室温制备[CF 2 CBrZnCl]（> 89％）中的溶液经由CF的原位金属化实现3 CH 2 Br或CF 2中的ZnCl的存在CHBr用LDA 2。钯催化此锌试剂与芳基碘化物的交叉偶联提供了α溴-β，β-trifluorostyrenes（ArCBrCF 2）在64-86％的分离产率，以基本上“一锅煮”过程。
• New Efficient Approach to 2,2-Diaryl-1,1-difluoro-1-alkenes and 1,1-Difluoro-2-aryl-1,3-dienes via Suzuki Coupling of α-Halo-β,β-difluorostyrenes
  作者：Anilkumar Raghavanpillai、Donald J. Burton

  DOI：10.1021/jo051842p

  日期：2006.1.1

  [Graphics]a-Halo-beta,beta-difluorostyrenes [ArCX = CF2; X = Br, I; Ar = aryl, heteroaryl; synthesized by the Pd(0)-catalyzed coupling reaction of the corresponding alpha-halo-beta,beta-difluoroethenylzinc reagents (CF2=CXZnCl, X = Br, I) with aryl iodides] were functionalized at the halogen site with arylboronic acids under Pd(0)-catalyzed Suzuki-Miyaura coupling reaction conditions to obtain 2,2-diaryl-1,1-difluoro-1-alkenes (ArAr'C=CF2, Ar' = aryl, heteroaryl) in 51-91% isolated yield. The corresponding reaction with alkenylboronic acids produced 1,1-difluoro-2-aryl-1,3-dienes in 53-80% isolated yield. Alternatively, 2,2-disubstituted-1,1-difluoro-1-alkenes were synthesized in moderate yield by a zinc-insertion reaction at the halogen site of the alpha-halo-beta,beta-difluorostyrenes, followed by Pd(0)-catalyzed cross-coupling of the zinc reagent with aryl or alkenyl iodides.