potassium (hex-5-enyloxy)methyltrifluoroborate | 1027642-32-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: potassium (hex-5-enyloxy)methyltrifluoroborate
• 英文别名: Potassium;trifluoro(hex-5-enoxymethyl)boranuide
• CAS: 1027642-32-5
• 化学式: C₇H₁₃BF₃O*K
• 分子量: 220.084
• InChiKey: BCCLJDASBFJZAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.25
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)吡咯 、 potassium (hex-5-enyloxy)methyltrifluoroborate 在 9-borabicyclo[3.3.1]nonane dimer 、 potassium fluoride 、 palladium diacetate 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以65%的产率得到potassium (6-(4-(1H-pyrrol-1-yl)phenyl)hexyloxy)methyltrifluoroborate
  参考文献：
  名称：

  Orthogonal Reactivity in Boryl-Substituted Organotrifluoroborates

  摘要：

  A method was developed for the hydroboration of alkenyl-containing organotrifluoroborates to generate dibora intermediates. The reactivity differences between organotrifluoroborates and trialkylboranes facilitated the cross-coupling of the borane moiety of these intermediates in a highly chemoselective fashion with aryl halides, leaving the trifluoroborate intact for subsequent transformation. A one-pot hydroboration/two-directional cross-coupling sequence was also demonstrated, providing the fully elaborated products in good yields. These conditions were also amenable in the cross-coupling of trialkylboranes to halo-containing organotrifluoroborates. The stability of the trifluoroborate moiety to these conditions allows simple and efficient strategies for complex molecule construction.

  DOI：

  10.1021/ja807076d
• 作为产物：
  描述：

  (溴甲基)三氟硼酸钾 、 5-己烯-1-醇 在 sodium hydride 、 potassium hydrogen bifluoride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 以84%的产率得到potassium (hex-5-enyloxy)methyltrifluoroborate
  参考文献：
  名称：

  烷氧基甲基三氟硼酸钾的制备及其与芳基氯的交叉偶联。

  摘要：

  通过用各种醇盐对溴甲基三氟硼酸钾进行 SN2 置换，以优异的产率制备了多种烷氧基甲基三氟硼酸盐底物。这些烷氧基甲基三氟硼酸盐与几种芳基氯有效地交叉偶联。这种方法提供了一种独特的不协调断开，允许在设计新的和改进的合成途径时具有更大的灵活性。

  DOI：

  10.1021/ol800532p

文献信息

• Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones
  作者：Javad Amani、Esmat Sodagar、Gary A. Molander

  DOI：10.1021/acs.orglett.5b03705

  日期：2016.2.19

  A visible-light, single-electron-transfer (SET), photoredox cross-coupling for the synthesis of α-alkoxyketones has been developed. In this method, various aliphatic and aromatic acyl chlorides were successfully coupled with structurally diverse potassium alkoxymethyltrifluoroborates, producing the corresponding α-alkoxyketones with high yields. In this operationally simple and mild cross-coupling

  已经开发了用于合成α-烷氧基酮的可见光，单电子转移（SET），光氧化还原交叉偶联。在这种方法中，成功地将各种脂肪族和芳香族酰氯与结构多样的烷氧基甲基三氟硼酸钾偶联，从而以高收率生产出相应的α-烷氧基酮。在这种操作简单且温和的交叉偶联方案中，所需的酮可通过一种对烷基硼化学和光氧化还原/ Ni催化均具有独特作用的键合连接，从稳定的起始原料中一步获得所需的酮。
• Synthesis of α-Fluoro-α-amino Acid Derivatives via Photoredox-Catalyzed Carbofluorination
  作者：Jaehoon Sim、Mark W. Campbell、Gary A. Molander

  DOI：10.1021/acscatal.8b04284

  日期：2019.2.1

  A mild, metal-free, regioselective carbofluorination of dehydroalanine derivatives has been developed. Alkyl radicals resulting from visible-light photoredox catalysis engage in a radical conjugate addition to dehydroalanine, with subsequent fluorination of the newly generated radical to afford an α-fluoro-α-amino acid. By using a highly oxidizing organic photocatalyst, this process incorporates non-stabilized

  已经开发出温和的，无金属的区域选择性碳氟化的脱氢丙氨酸衍生物。由可见光光氧化还原催化产生的烷基自由基与脱氢丙氨酸加成自由基共轭物，随后对新产生的自由基进行氟化，得到α-氟-α-氨基酸。通过使用高度氧化的有机光催化剂，该方法结合了衍生自可商购获得的烷基三氟硼酸酯的不稳定的伯，仲和叔烷基，以提供各种氟化的非天然氨基酸。
• Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers
  作者：Idris Karakaya、David N. Primer、Gary A. Molander

  DOI：10.1021/acs.orglett.5b01463

  日期：2015.7.2

  Single-electron transmetalation has emerged as an enabling paradigm for the cross-coupling of C-sp(3) hybridized organotrifluoroborates. Cross-coupling of alpha-alkoxymethyl-trifluoroborates with aryl and heteroaryl bromides has been demonstrated by employing dual catalysis with a combination of an iridium photoredox catalyst and a Ni cross-coupling catalyst. The resulting method enables the alkoxymethylation of diverse (hetero)arenes under mild, room-temperature conditions.