1-(4-methyl-benzenesulfonyl)indole-5-boronic acid | 851524-84-0

• 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-(4-methyl-benzenesulfonyl)indole-5-boronic acid
• 英文别名: 1-(4-methylbenzene-sulfonyl)indol-5-boronic acid；(1-tosyl-1H-indol-5-yl)boronic acid；[1-(4-methylphenyl)sulfonylindol-5-yl]boronic acid
• CAS: 851524-84-0
• 化学式: C₁₅H₁₄BNO₄S
• 分子量: 315.157
• InChiKey: SKPQSSRVOAEOSO-UHFFFAOYSA-N

物化性质

• 沸点：
  581.5±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  87.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-溴苯甲醚 、 1-(4-methyl-benzenesulfonyl)indole-5-boronic acid 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 以10%的产率得到1-(p-toluenesulfonyl)-5-(4-methoxyphenyl)indole
  参考文献：
  名称：

  Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection

  摘要：

  Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential to ensuring optimum results in these Suzuki couplings. These results may also be relevant to couplings involving other substrates.

  DOI：

  10.1021/jo0491612
• 作为产物：
  描述：

  N-tosyl-5-bromoindole 在 potassium hydride 、 叔丁基锂 、 硼酸三甲酯 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 0.43h， 生成 1-(4-methyl-benzenesulfonyl)indole-5-boronic acid
  参考文献：
  名称：

  Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection

  摘要：

  Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential to ensuring optimum results in these Suzuki couplings. These results may also be relevant to couplings involving other substrates.

  DOI：

  10.1021/jo0491612

文献信息

• Hydroxylamine Umpolung in Copper-Catalyzed Cross-Coupling Reactions to Synthesize <i>N</i>-Arylhydroxylamine Derivatives
  作者：Gary Mathieu、Emna Azek、Calvine Lai、Hélène Lebel

  DOI：10.1021/acscatal.3c06020

  日期：2024.4.5

  chemistry to synthesize a reagent for the transfer of an electrophilic N–O moiety. Reagent 2 is a hydroxylamine umpolung that allows the formation of highly valuable N-arylhydroxylamine synthons via a copper-catalyzed cross-coupling reaction with boronic acids. The process with reagent 2 showed a wide functional group tolerance, especially with other electrophilic functional groups, and exhibited an orthogonal

  羟胺衍生物是成熟的氮前体，可通过氮-氧键的断裂经历各种过渡金属催化的转化。相反，由于 N-O 键固有的脆弱性，含有可转移亲电子羟胺的试剂的开发一直难以实现。在此，我们展示了高价碘化学在合成用于亲电子 N-O 部分转移的试剂中的效用。试剂2是一种羟胺极化，可通过铜催化的与硼酸的交叉偶联反应形成高价值的N-芳基羟胺合成子。使用试剂2的方法显示出广泛的官能团耐受性，特别是对其他亲电官能团的耐受性，并且与合成N-芳基羟胺衍生物的其他方法相比表现出正交反应性。这些可以进行 Cope 重排和后官能化，提供各种含氮结构单元。实验和计算机机理研究提出了一种催化循环，其中第一步涉及形成铜（II）-羟胺物质。然后该物质与硼酸反应产生所需的产物。
• Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection
  作者：Mònica Prieto、Esther Zurita、Esmeralda Rosa、Lourdes Muñoz、Paul Lloyd-Williams、Ernest Giralt

  DOI：10.1021/jo0491612

  日期：2004.10.1

  Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential to ensuring optimum results in these Suzuki couplings. These results may also be relevant to couplings involving other substrates.