Abd El Sater Mariam, Mellah Mohamed, Dragoe Diana, Kolodziej Emilie, Jaber Nada, Schulz Emmanuelle
Equipe de Catalyse Moléculaire, Université Paris Saclay, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Bâtiment 420, 91405, Orsay Cedex, France.
Laboratoire de Chimie Médicinale et des Produits Naturels, Université Libanaise, Faculté des Sciences (I) et PRASE-EDST, postcode is missing, Hadath, Beyrouth, Lebanon.
Chemistry. 2021 Jun 25;27(36):9454-9460. doi: 10.1002/chem.202101003. Epub 2021 May 17.
The first immobilization of a pyrene-tagged chromium salen complex through π-π noncovalent interactions on reduced graphene oxide (rGO) is described. A very robust supported catalytic system is obtained to promote asymmetric catalysis in repeated cycles, without loss of activity or enantioselectivity. This specific behavior was demonstrated in two different catalytic reactions (up to ten reuses) promoted by chromium salen complexes, the cyclohexene oxide ring-opening reaction and the hetero-Diels-Alder cycloaddition between various aldehydes and Danishefsky's diene. Furthermore, the chiral chromium salen@rGO has been found to be compatible with a multi-substrate type use, in which the structure of the substrate involved is modified each time the catalyst is reused.
本文描述了通过芘标记的铬（Ⅲ）双水杨醛缩乙二胺配合物与还原氧化石墨烯（rGO）之间的π-π非共价相互作用实现的首次固定化。由此获得了一种非常稳定的负载型催化体系，可在重复循环中促进不对称催化反应，且活性和对映选择性均无损失。这种特殊性能在铬（Ⅲ）双水杨醛缩乙二胺配合物促进的两种不同催化反应（最多重复使用十次）中得到了证明，即环氧环己烷的开环反应以及各种醛与达尼谢夫斯基双烯之间的杂环狄尔斯-阿尔德环加成反应。此外，已发现手性铬（Ⅲ）双水杨醛缩乙二胺@rGO与多底物类型的使用兼容，即在每次重复使用催化剂时，所涉及底物的结构都会发生变化。
