Iridium-Catalyzed Carbonylative Synthesis of Halogen-Containing Quinolin-2(1H)-ones from Internal Alkynes and Simple Anilines was written by Zhu, Fengxiang;Li, Yahui;Wang, Zechao;Wu, Xiao-Feng. And the article was included in Advanced Synthesis & Catalysis in 2016.COA of Formula: C6H10O2 This article mentions the following:
In this communication, a novel and efficient iridium-catalyzed carbonylative annulation of simple anilines with internal alkynes for the straightforward synthesis of halogen-containing quinolin-2(1H)-ones, e.g., I has been developed. The reaction proceeds without preactivation and directing groups through direct N-H and C-H bond activation with a broad substrate scope and high efficiency. Halogen functional groups can be well tolerated here. Remarkably, this is the first example of an iridium-catalyzed carbonylative C-H activation of anilines. In the experiment, the researchers used many compounds, for example, 1,4-Dimethoxy-2-butyne (cas: 16356-02-8COA of Formula: C6H10O2).
1,4-Dimethoxy-2-butyne (cas: 16356-02-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Ethers feature bent C–O–C linkages. In dimethyl ether, the bond angle is 111° and C–O distances are 141 pm. The barrier to rotation about the C–O bonds is low. The bonding of oxygen in ethers, alcohols, and water is similar. In the language of valence bond theory, the hybridization at oxygen is sp3.COA of Formula: C6H10O2
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem