Girish Yarabhally R, Pandit Subrata, Pandit Subhendu, De Mrinmoy
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560012, Karnataka, India.
Chem Asian J. 2017 Sep 19;12(18):2393-2398. doi: 10.1002/asia.201701072. Epub 2017 Sep 4.
The Diels-Alder (DA) reaction, a [4+2] cycloaddition reaction, is highly important in synthetic organic chemistry and is frequently used in the synthesis of natural products containing six-membered rings. Herein, we report an efficient protocol for the DA reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two-dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy features of this protocol. The heterogeneous GO catalyst can be easily recovered and used multiple times without any significant loss in catalytic activity.
狄尔斯-阿尔德（DA）反应是一种[4+2]环加成反应，在有机合成化学中非常重要，常用于合成含六元环的天然产物。在此，我们报道了一种高效的方法，即在室温下的水介质中，使用二维氧化石墨烯（GO）作为多相碳催化剂，实现9-羟甲基蒽与N-取代马来酰亚胺之间的DA反应。该方法具有高收率、底物范围广、低温、优异的官能团耐受性、原子经济性以及水作为绿色溶剂等显著特点。多相GO催化剂易于回收且可多次使用，催化活性无明显损失。
