dibenzo[b,d]furan-1-yl pivalate | 1554400-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: dibenzo[b,d]furan-1-yl pivalate
• 英文别名: dibenzo[b,d]furan-4-yl pivalate；Dibenzofuran-4-yl 2,2-dimethylpropanoate
• CAS: 1554400-55-3
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: VFHNDDJDAKKPNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  triethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane 、 dibenzo[b,d]furan-1-yl pivalate 在 copper (II)-fluoride 、 bis(1,5-cyclooctadiene)nickel (0) 、 cesium fluoride 、 三环己基膦 作用下， 以 甲苯 为溶剂， 生成 dibenzo[b,d]furan-1-yltriethylsilane
  参考文献：
  名称：

  A Mild Ni/Cu-Catalyzed Silylation via C–O Cleavage

  摘要：

  A Ni/Cu-catalyzed silylation of unactivated C-O electrophiles derived from phenols or benzyl alcohols is described. This transformation is characterized by its wide scope and mild conditions, providing a direct access to synthetically versatile silylated compounds. The protocol allows for the coupling of C(sp(2))-O and even C(sp(3))-O bonds with similar efficiency.

  DOI：

  10.1021/ja412107b
• 作为产物：
  描述：

  4-二苯并呋喃醇 、 三甲基乙酸酐 在 iron(III) chloride 作用下， 以 neat (no solvent) 为溶剂， 生成 dibenzo[b,d]furan-1-yl pivalate
  参考文献：
  名称：

  A Mild Ni/Cu-Catalyzed Silylation via C–O Cleavage

  摘要：

  A Ni/Cu-catalyzed silylation of unactivated C-O electrophiles derived from phenols or benzyl alcohols is described. This transformation is characterized by its wide scope and mild conditions, providing a direct access to synthetically versatile silylated compounds. The protocol allows for the coupling of C(sp(2))-O and even C(sp(3))-O bonds with similar efficiency.

  DOI：

  10.1021/ja412107b

文献信息

• Ni-Catalyzed Stannylation of Aryl Esters via C−O Bond Cleavage
  作者：Yiting Gu、Rúben Martín

  DOI：10.1002/anie.201611720

  日期：2017.3.13

  Ni‐catalyzed stannylation of aryl esters with air‐ and moisture‐insensitive silylstannyl reagents via C −O cleavage is described. This protocol is characterized by its wide scope, including challenging combinations, thus enabling access to versatile building blocks and orthogonal C−heteroatom bond formations.

  描述了一种通过空气 裂解对水和不敏感的甲硅烷基锡烷基转移试剂进行镍催化的芳基酯的锡烷基化反应。该协议的特点是适用范围广，包括具有挑战性的组合，因此可以访问通用的构建基块和正交的C-杂原子键形成。
• Copper-Mediated Functionalization of Aryl Trifluoroborates
  作者：Melanie Sanford、Sydonie Schimler

  DOI：10.1055/s-0035-1562529

  日期：——

  trifluoroborates with tetrabutylammonium or alkali metal salts to form C–O, C–N, and C–halogen bonds. The reactions proceed under mild conditions (often room temperature over 16 hours) with carboxylate, halide, and azide salts, all nucleophiles that have been underrepresented in the copper cross-coupling literature. Preliminary results show that copper salts bearing weakly coordinating X-type ligands

  本文描述了 Cu(OTf)2 介导的芳基和杂芳基三氟硼酸盐与四丁基铵或碱金属盐的偶联，形成 C-O、C-N 和 C-卤素键。反应在温和条件下进行（通常在室温下超过 16 小时），使用羧酸盐、卤化物和叠氮化物，所有亲核试剂在铜交叉偶联文献中都没有得到充分体现。初步结果表明，带有弱配位 X 型配体的铜盐对于使这些转化在温和条件下进行是必不可少的。
• 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。
• Chromium-Catalyzed Selective Borylation of Vinyl Triflates and Unactivated Aryl Carboxylic Esters with Pinacolborane
  作者：Li Gong、Chao Li、Fangyan Yuan、Senlin Liu、Xiaoming Zeng

  DOI：10.1021/acs.orglett.2c01015

  日期：2022.5.6

  catalysis via the selective formation of vinyl and aryl boronate esters. The competing hydrided reduction or allylic borylation proceeds sluggishly or does not occur, therefore providing a selective strategy for the incorporation of boronate into olefins and arenes. Mechanistic studies indicate that the σ-bond metathesis or oxidative addition mechanism may be considered to be responsible for the cleavage

  使用频哪醇硼烷对丰富的乙烯基三氟甲磺酸酯和未活化的芳基羧酸酯进行硼酸化是通过铬催化选择性形成乙烯基和芳基硼酸酯实现的。竞争性氢化还原或烯丙基硼化反应缓慢或不发生，因此为将硼酸盐结合到烯烃和芳烃中提供了一种选择性策略。机理研究表明，σ键复分解或氧化加成机制可能被认为是酯支架断裂的原因。