Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba 6-3, Aramaki, Aoba-ku, Sendai, Miyagi, 980-8578, Japan.
Chemistry. 2020 Dec 4;26(68):15793-15798. doi: 10.1002/chem.202001961. Epub 2020 Oct 6.
An aerobic dehydrogenation of nitrogen-containing heterocycles catalyzed by Grubbs catalyst is developed. The reaction is applicable to various nitrogen-containing heterocycles. The exceptionally high functional group compatibility of this method was confirmed by the oxidation of an unprotected dihydroindolactam V to indolactam V. Furthermore, by taking advantage of the oxygen-mediated structural change of the Grubbs catalyst, we integrated ring-closing metathesis and subsequent aerobic dehydrogenation to develop the novel assisted-tandem catalysis using molecular oxygen as a chemical trigger. The utility of the assisted-tandem catalysis was demonstrated by the concise synthesis of N-containing fused heteroarenes including a natural antibiotic, pyocyanine.
开发了一种由 Grubbs 催化剂催化的含氮杂环的需氧脱氢反应。该反应适用于各种含氮杂环。该方法具有极高的官能团相容性，通过未保护的二氢吲哚啉 V 的氧化即可证实这一点，可将其氧化为吲哚啉 V。此外，通过利用 Grubbs 催化剂的氧介导结构变化，我们将闭环复分解反应和随后的需氧脱氢反应集成在一起，利用分子氧作为化学引发剂，开发了新型的辅助串联催化。该辅助串联催化的实用性通过包括天然抗生素绿脓菌素在内的含 N 稠合杂芳烃的简洁合成都得到了证明。
