1-(1-fluoro-2,2-diiodovinyl)-4-methylbenzene | 1420041-79-7

• 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: 1-(1-fluoro-2,2-diiodovinyl)-4-methylbenzene
• CAS: 1420041-79-7
• 化学式: C₉H₇FI₂
• 分子量: 387.962
• InChiKey: DNCOIBYFSOXNHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1-(1-fluoro-2,2-diiodovinyl)-4-methylbenzene 、 对氯苯基三甲氧基硅烷 在 三乙烯二胺 、 四丁基氟化铵 、 palladium diacetate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 20.0h， 以74%的产率得到(Z)-1-chloro-4-(2-fluoro-2-(p-tolyl)vinyl)benzene
  参考文献：
  名称：

  Silver-Mediated Decarboxylative Fluorodiiodination of Alkynoic Acids: Synthesis of Regio- and Stereoselective Fluoroalkenes

  摘要：

  A variety of arylalkynoic acids reacted with 1,3-diiodo-5,5-dimethylhydantoin and HF.pyridine in the presence of AgOAc to provide the corresponding 1-fluoro-2,2-diiodovinylarenes in good yields and high regioselectivity. In addition, Pd-catalyzed cross-coupling reaction of 1-fluoro-2,2-diiodovinylarenes afforded diaryl coupling products in the Suzuki reaction and monoaryl coupling products with high stereo-selectivity in the Hiyama reaction. It was found that C-F-activated borylation of fluoroalkenes using Pd catalyst afforded the vinylboranes with good yields.

  DOI：

  10.1021/acs.orglett.9b00597
• 作为产物：
  描述：

  3-(4-甲基苯基)丙-2-炔酸 在 1,3-二碘-5,5-二甲基海因 、 silver(I) acetate 、 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以80%的产率得到1-(1-fluoro-2,2-diiodovinyl)-4-methylbenzene
  参考文献：
  名称：

  Silver-Mediated Decarboxylative Fluorodiiodination of Alkynoic Acids: Synthesis of Regio- and Stereoselective Fluoroalkenes

  摘要：

  A variety of arylalkynoic acids reacted with 1,3-diiodo-5,5-dimethylhydantoin and HF.pyridine in the presence of AgOAc to provide the corresponding 1-fluoro-2,2-diiodovinylarenes in good yields and high regioselectivity. In addition, Pd-catalyzed cross-coupling reaction of 1-fluoro-2,2-diiodovinylarenes afforded diaryl coupling products in the Suzuki reaction and monoaryl coupling products with high stereo-selectivity in the Hiyama reaction. It was found that C-F-activated borylation of fluoroalkenes using Pd catalyst afforded the vinylboranes with good yields.

  DOI：

  10.1021/acs.orglett.9b00597

文献信息

• Silver-Assisted Difunctionalization of Terminal Alkynes: Highly Regio- and Stereoselective Synthesis of Bromofluoroalkenes
  作者：Yibiao Li、Xiaohang Liu、Deyun Ma、Bifu Liu、Huanfeng Jiang

  DOI：10.1002/adsc.201200250

  日期：2012.10.8

  The difunctionalization of terminal alkynes was achieved with silver fluoride (AgF) and N-bromosuccinimide (NBS) as halogen sources. The presence of the halide moiety greatly enhances the reactivity of the vinyl fluoride compounds that can probably can be transformed into various products that are difficult or even impossible to obtain via direct fluorination. Meanwhile, the monofluoro<.>alkenes were

  用氟化银（AgF）和N-溴琥珀酰亚胺（NBS）作为卤素源可实现末端炔烃的双官能化。卤化物部分的存在极大地增强了氟乙烯化合物的反应性，该氟乙烯化合物很可能可以转化为通过直接氟化难以或什至不可能获得的各种产物。同时，单氟<>烯烃均轻便合成通过使用如AGF以良好产率氟化剂缺电子CC三键的高度化疗和区域选择性氟化。
• Selective Synthesis of (<i>Z</i>)- and (<i>E</i>)-β-Fluoro-α,β-Unsaturated Amides Using Palladium-Catalyzed Aminocarbonylation
  作者：Su Hyeon Park、Sunwoo Lee

  DOI：10.1021/acs.orglett.3c02809

  日期：2023.9.22

  The selective synthesis of (Z)- and (E)-β-fluoro-α,β-unsaturated amides via the palladium-catalyzed aminocarbonylation of 1-fluoro-2,2-diiodovinylarenes is described in the present study. Using Pd(allyl)Cl}2 as a catalyst and DBU as a base in DMF, the primary product is (Z)-isomers. Conversely, the use of a Xantphos ligand along with Pd(allyl)Cl}2 and Et3N as the bases in 1,4-dioxane leads to the

  本研究描述了通过钯催化的 1-氟-2,2-二碘乙烯基芳烃的氨基羰基化选择性合成( Z )-和 ( E )-β-氟-α,β-不饱和酰胺。在DMF中以Pd(烯丙基)Cl} 2为催化剂，DBU为碱，主要产物为( Z )-异构体。相反，在1,4-二恶烷中使用Xantphos配体以及Pd(烯丙基)Cl} 2和Et 3 N作为碱导致( E )-异构体的选择性形成。值得注意的是，苯环上带有各种取代基的1-氟-2,2-二碘乙烯基芳烃与各种仲胺反应，以高产率和选择性生成相应的( Z )-异构酰胺。相反，( E )-异构酰胺表现出较低的产率和有限的适用性。