Palladium-Catalyzed Dual Annulation: A Method for the Synthesis of Norneocryptolepine was written by Yeh, Li-Hsuan;Wang, Hung-Kai;Pallikonda, Gangaram;Ciou, Yu-Lun;Hsieh, Jen-Chieh. And the article was included in Organic Letters in 2019.Electric Literature of C8H9NO3 This article mentions the following:
A novel procedure for the Pd-catalyzed dual annulation reaction of I and derivatives to synthesize the norneocryptolepine derivatives involving the concerted construction of two central heterocycles is reported. The further methylation of norneocryptolepine (II) to afford its alkaloid analog neocryptolepine implies that synthesis of various neocryptolepine derivatives is feasible. The oxidative addition of Pd(0) is indicated as the key step to activate the intramol. addition of nitrile according to the mechanism study. In the experiment, the researchers used many compounds, for example, 3-Methyl-4-nitroanisole (cas: 5367-32-8Electric Literature of C8H9NO3).
3-Methyl-4-nitroanisole (cas: 5367-32-8) belongs to ethers. The oxygen atom in ethers are more electronegative than carbon, thus the hydrogens which are alpha to the ethers are more acidic than the simple hydrocarbons. The unique properties of ethers (i.e., that they are strongly polar, with nonbonding electron pairs but no hydroxyl group) enhance the formation and use of many reagents. For example, Grignard reagents cannot form unless an ether is present to share its lone pair of electrons with the magnesium atom. Complexation of the magnesium atom stabilizes the Grignard reagent and helps to keep it in solution.Electric Literature of C8H9NO3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem