The synthesis of pyrroles via acceptorless dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols mediated by a robust and reusable catalyst based on nanometer-sized iridium particles
The synthesis of pyrroles via acceptorless dehydrogenative condensation of secondary alcohols and 1,2-amino alcohols mediated by a robust and reusable catalyst based on nanometer-sized iridium particles
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DOI：
10.1039/c4cy01018c
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发表时间：
2014-01-01
影响因子：
5
通讯作者：
Kempe, Rhett
中科院分区：
文献类型：
--
作者：
Forberg, Daniel;Obenauf, Johannes;Kempe, Rhett
吡咯是一种重要的化合物，在医药和材料科学中有着广泛的应用。它们可以由仲醇和氨基醇可持续地合成。在这个反应过程中释放出氢和水。在这里，我们提出，这种可持续的催化吡咯合成可以有效地介导一种新的铱纳米粒子催化剂。催化剂合成从分子前体、N-配体稳定的Ir络合物和市售的聚硅氮烷开始。实现了纳米尺寸的铱颗粒的产生（由于在载体中存在N原子）。载体的坚固性质允许催化剂的重复使用。通过23个吡咯衍生物的合成（高达93%的分离产率）验证了反应的范围。因此，可以观察到有吸引力的官能团耐受性（例如胺和烯烃）。市售的非均相Ir催化剂在该吡咯合成中效率低，并且在可重复使用性方面极其有限。
Pyrroles are important compounds with several applications in medicine and material science. They can be synthesized sustainably from secondary alcohols and amino alcohols. Hydrogen and water are liberated in the course of this reaction. Here, we present that this sustainable catalytic pyrrole synthesis can be mediated efficiently by a novel iridium nanoparticle catalyst. The catalyst synthesis starts from molecular precursors, an N-ligand stabilized Ir complex and a commercially available polysilazane. The generation of nanometer-sized iridium particles was achieved (due to the presence of N atoms in the support). The robust nature of the support allows reuse of the catalyst. The scope of the reaction was verified by the synthesis of 23 pyrrole derivatives (up to 93% isolated yield). Thus, an attractive functional group tolerance (e.g. amines and olefins) could be observed. Commercially available heterogeneous Ir catalysts are inefficient in this pyrrole synthesis and extremely limited in terms of reusability.