2-deuterio-naphthalene | 2430-34-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-deuterio-naphthalene
• 英文别名: naphthalene-2-d；2-deuteronaphthalene；2-deuterionaphthalene
• CAS: 2430-34-4
• 化学式: C₁₀H₈
• 分子量: 129.166
• InChiKey: UFWIBTONFRDIAS-MICDWDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-deuterio-naphthalene 在 氨 、 potassium amide 作用下， 生成 萘
  参考文献：
  名称：

  摘要：

  The kinetic isotope effects in deuterium and tritium exchange in benzene, fluorobenzene, pyridine, pyridine N-oxide, and quinoline with a solution of an alkali metal amide in liquid ammonia k(D)(NH3)/k(T)(NH3) were determined, where k(D)(NH3) and k(T)(NH3) are the experimental rate constants of protodedeuteration and protodetritiation, respectively. The variation of the tritium exchange rates in benzene in going from NH3 to ND3 (k(T)(NH3) and k(T)(ND3)) was evaluated. The deviation of the observed ratios k(D)(NH3)/k(T)(NH3) and k(H)(ND3)/k(T)(ND3) from the maximum possible values corresponding to the Swan-Shaad equation suggests the reaction mechanism in which both elementary stages, ionization of the CH acid and diffusion separation of the complex of the carbanion with the ammonia molecule, are partially limiting. A small decrease in the secondary isotope effect of the solvent, defined as k(T)(ND3)/k(T)(NH3) as compared to the theoretical maximum of 2.4, is assumed to be due to similar structures of the transition state and the equilibrium carbanion. A theoretical explanation was given for the observed dependences of the primary isotope effect of the substrate on pK(a) for deutero (tritio) derivatives of fluorobenzene [4D(t) < 3D(t) < 2D(t)], for reactions in the series pyridine-2D(t) < pyridine-3D(t) < quinoline3D(t), and for hydrogen exchange in pyridine-2D(t) N-oxide (k(D)(NH3)/k(T)(NH3) similar to 1).

  DOI：

  10.1023/a:1013134511332
• 作为产物：
  描述：

  2-萘甲醚 在 bis(1,5-cyclooctadiene)nickel (0) 、 三乙基(硅烷-d) 、 三环己基膦 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以93%的产率得到2-deuterio-naphthalene
  参考文献：
  名称：

  Ni-Catalyzed Reduction of Inert C−O Bonds: A New Strategy for Using Aryl Ethers as Easily Removable Directing Groups

  摘要：

  An efficient Ni-catalyzed protocol for the reductive cleavage of inert C-O bonds has been developed. The method is characterized by its simplicity and wide scope, thereby allowing the use of aryl ethers as easily removable directing groups in organic synthesis.

  DOI：

  10.1021/ja106943q

文献信息

• Efficient and selective hydrogenation of C–O bonds with a simple sodium formate catalyzed by nickel
  作者：Xiaoxiang Xi、Tieqiao Chen、Ji-Shu Zhang、Li-Biao Han

  DOI：10.1039/c7cc08709h

  日期：——

  A Ni-catalyzed hydrogenation of C–O compounds with sodium formate is developed. Various esters, i.e. aryl, alkenyl, benzyl pivalates, and even the aryl ethers, were efficiently reduced with a loading of nickel catalysts down to 0.5 mol%. Reactive functional groups such as C–C double bonds, carbonyl, CN, MeS and halogen groups are tolerable. This reaction can be used for the modification of complex

  开发了镍催化的甲酸钠对C–O化合物的加氢反应。各种催化剂，即芳基，烯基，新戊酸苄基酯，甚至芳基醚，都可以通过将镍催化剂的负载量降至0.5 mol％有效地还原。反应性官能团，例如CC双键，羰基，CN，MeS和卤素基团是可以忍受的。该反应可用于复杂分子的修饰并大规模进行。
• Nickel-catalyzed decyanation of inert carbon–cyano bonds
  作者：Tuhin Patra、Soumitra Agasti、Akanksha、Debabrata Maiti

  DOI：10.1039/c2cc36883h

  日期：——

  Nickel catalyzed decyanation of aryl and aliphatic cyanides with hydrosilane as the hydride source has been developed. This method is easy to handle, scalable and can be carried out without a glove box. The method has been applied in the cyanide directed functionalization reaction and α-substitution of benzyl cyanide.

  镍催化的芳基和脂肪族氰化物的脱氰化反应已发展起来，以氢硅烷作为氢源。这种方法易于操作、可扩展，并且无需在手套箱中进行。该方法已被应用于氰基导向的功能化反应以及苄基氰的α-取代反应中。
• Nickel-Catalyzed Photodehalogenation of Aryl Bromides
  作者：Ruben Martin、Bradley Higginson、Jesus Sanjosé-Orduna、Yiting Gu

  DOI：10.1055/a-1457-2399

  日期：2021.10

  Herein, we describe a Ni-catalyzed photodehalogenation of aryl bromides under visible light irradiation that utilizes tetrahydrofuran as hydrogen source. The protocol obviates the need for exogeneous amine reductants or photocatalysts, and is characterized by its simplicity and broad scope, including challenging substrate combinations

  在这里，我们描述了在利用四氢呋喃作为氢源的可见光照射下镍催化的芳基溴化物的光脱卤。该方案消除了对外源胺还原剂或光催化剂的需求，其特点是简单易行且适用范围广，包括具有挑战性的底物组合
• A visible-light-photocatalytic water-splitting strategy for sustainable hydrogenation/deuteration of aryl chlorides
  作者：Xiang Ling、Yangsen Xu、Shaoping Wu、Mofan Liu、Peng Yang、Chuntian Qiu、Guoqiang Zhang、Hongwei Zhou、Chenliang Su

  DOI：10.1007/s11426-019-9672-8

  日期：2020.3

  chlorides instead of using flammable H2. When applying heavy water-splitting systems, we could selectively install deuterium at the C−Cl position of aryl chlorides under mild conditions for the sustainable synthesis of high-valued added deuterated chemicals. Sub-micrometer Pd nanosheets (Pd NSs) decorated crystallined polymeric carbon nitrides (CPCN) is developed as the bifunctional photocatalyst,

  摘要 氯化碳（C-Cl）键的加氢/氘化具有很高的意义，但在合成化学中仍然是一个巨大的挑战，特别是使用安全且廉价的氢供体。在本文中，提出了一种可见光光催化水分解加氢技术（WSHT）来原位生成用于控制芳基氯化物氢化的活性H物种（即H ad），而不是使用易燃的H 2。当使用重水分解系统时，我们可以在温和的条件下选择性地将氘安装在芳基氯化物的C-Cl位置，以可持续合成高价值的氘代化学品。亚微米级的Pd纳米片（Pd NSs）装饰的结晶聚合碳氮化物（CPCN）被开发为双功能光催化剂，而Pd NSs不仅充当CPCN的助催化剂，以生成和稳定H（D）物种，而且还起着重要的作用。 C-Cl键的顺序活化和加氢/氘化中的作用。本文重点介绍了可控制低成本芳基氯化物加氢/氘代的光催化WSHT，为高附加值化学物质的光合作用提供了一种有前途的方法，而不是产生了氢。
• Chemoselective Cross-Coupling between Two Different and Unactivated C(aryl)–O Bonds Enabled by Chromium Catalysis
  作者：Jinghua Tang、Liu Leo Liu、Shangru Yang、Xuefeng Cong、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/jacs.0c00283

  日期：2020.4.29

  combination of low-cost Cr(II) salt, 4,4-di-tert-butyl-2,2-dipyridyl (dtbpy) ligand and magnesium reductant shows high reactivity in promoting the reductive cross-coupling of aryl methyl ether derivatives with aryl esters, by cleavage and coupling of two different C(aryl)-O bonds under mild conditions. The formation of active low-valent Cr species by reduction of CrCl2 with Mg can be considered, which prefers

  我们在这里报告了两个不同且未活化的 C(芳基)-O 键与铬催化之间交叉耦合的第一个例子。低成本的 Cr(II) 盐、4,4-二叔丁基-2,2-二吡啶基 (dtbpy) 配体和镁还原剂的组合在促进芳基甲基醚衍生物与芳基酯，通过在温和条件下裂解和偶联两个不同的 C(芳基)-O 键。可以考虑通过用 Mg 还原 CrCl2 形成活性低价 Cr 物种，它更喜欢在 dtbpy 和邻亚氨基助剂的螯合帮助下最初激活苯基甲基醚的 C(芳基)-O 键。随后的连续还原、第二次 C(芳基)-O 活化和还原消除允许实现 C(芳基)-O/C(芳基)-O 键的选择性交叉偶联。