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Quaternary ammonium hydroxide‐functionalized g‐C3N4 catalyst for aerobic hydroxylation of arylboronic acids to phenols
Journal of the Chinese Chemical Society ( IF 1.6 ) Pub Date : 2020-07-07 , DOI: 10.1002/jccs.202000141 Ibrahim Muhammad 1 , Subramaniyan Mannathan 2 , Manickam Sasidharan 1
Journal of the Chinese Chemical Society ( IF 1.6 ) Pub Date : 2020-07-07 , DOI: 10.1002/jccs.202000141 Ibrahim Muhammad 1 , Subramaniyan Mannathan 2 , Manickam Sasidharan 1
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A new and efficient metal‐free approach toward the synthesis of phenols via an aerobic hydroxylation of arylboronic acids by using a novel quaternary ammonium hydroxide g‐C3N4 catalyst has been described. The functionalized quaternary ammonium hydroxide (g‐C3N4‐OH) has been prepared from graphitic carbon nitride (g‐C3N4) scaffold by converting the residual –NH2 and –NH groups to quaternary methyl ammonium iodide by performing a methylation reaction with methyl iodide followed by ion‐exchange with 0.1 N KOH or anion exchange resin Amberlyst A26 (OH‐ form) by post‐synthetic modification. The resultant g‐C3N4‐OH was characterized by XRD, FTIR, field‐emission scanning electron microscope (FESEM), high‐resolution transmission electron microscope (HRTEM), N2 adsorption/desorption isotherms, and acid–base titration. Tested as solid‐base catalysts, the g‐C3N4‐OH showed excellent catalytic activity in the aerobic hydroxylation reaction by converting a variety of arylboronic acids to the corresponding phenols in high yields. More importantly, the g‐C3N4‐OH solid‐base has been successfully reused four times with the minor loss of initial catalytic activity (10.5%).
中文翻译：
季铵氢氧化物官能化的g-C3N4催化剂，用于芳基硼酸好氧羟基化为苯酚
本文描述了一种新型高效的无金属方法，该方法通过使用新型氢氧化季铵g-C 3 N 4催化剂通过芳基硼酸的好氧羟基化来合成苯酚。功能化的季铵氢氧化物（g-C 3 N 4 -OH）是由石墨氮化碳（g-C 3 N 4）支架通过将残留的-NH 2和-NH基团转化为季甲基碘化铵而制得的与甲基碘发生甲基化反应，然后通过合成后修饰与0.1 N KOH或阴离子交换树脂Amberlyst A26（OH-形式）进行离子交换。最终的g‐C 3 N 4‐OH的特征在于XRD，FTIR，场发射扫描电子显微镜（FESEM），高分辨率透射电子显微镜（HRTEM），N 2吸附/解吸等温线和酸碱滴定法。经测试为固体碱催化剂，g-C 3 N 4 -OH在需氧羟基化反应中表现出优异的催化活性，该反应可将各种芳基硼酸高产率地转化为相应的苯酚。更重要的是，g-C 3 N 4 -OH固体碱已成功重复使用了四次，而初始催化活性损失很小（10.5％）。
更新日期：2020-08-11
中文翻译：
季铵氢氧化物官能化的g-C3N4催化剂，用于芳基硼酸好氧羟基化为苯酚
本文描述了一种新型高效的无金属方法，该方法通过使用新型氢氧化季铵g-C 3 N 4催化剂通过芳基硼酸的好氧羟基化来合成苯酚。功能化的季铵氢氧化物（g-C 3 N 4 -OH）是由石墨氮化碳（g-C 3 N 4）支架通过将残留的-NH 2和-NH基团转化为季甲基碘化铵而制得的与甲基碘发生甲基化反应，然后通过合成后修饰与0.1 N KOH或阴离子交换树脂Amberlyst A26（OH-形式）进行离子交换。最终的g‐C 3 N 4‐OH的特征在于XRD，FTIR，场发射扫描电子显微镜（FESEM），高分辨率透射电子显微镜（HRTEM），N 2吸附/解吸等温线和酸碱滴定法。经测试为固体碱催化剂，g-C 3 N 4 -OH在需氧羟基化反应中表现出优异的催化活性，该反应可将各种芳基硼酸高产率地转化为相应的苯酚。更重要的是，g-C 3 N 4 -OH固体碱已成功重复使用了四次，而初始催化活性损失很小（10.5％）。
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