Ni-Catalyzed Reductive Coupling of Electron-Rich Aryl Iodides with Tertiary Alkyl Halides was written by Wang, Xuan;Ma, Guobin;Peng, Yu;Pitsch, Chloe E.;Moll, Brenda J.;Ly, Thu D.;Wang, Xiaotai;Gong, Hegui. And the article was included in Journal of the American Chemical Society in 2018.Synthetic Route of C8H9IO This article mentions the following:
This work illustrates the reductive coupling of electron-rich aryl halides with tertiary alkyl halides under Ni-catalyzed cross-electrophile coupling conditions, which offers an efficient protocol for the construction of all carbon quaternary stereogenic centers. The mild and easy-to-operate reaction tolerates a wide range of functional groups. The utility of this method is manifested by the preparation of cyclotryptamine derivatives, wherein successful incorporation of 7-indolyl moieties is of particular interest as numerous naturally occurring products are composed of these key scaffolds. DFT calculations have been carried out to investigate the proposed radical chain and double oxidative addition pathways, which provide useful mechanistic insights into the part of the reaction that takes place in solution In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Synthetic Route of C8H9IO).
4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) 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. 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.Synthetic Route of C8H9IO
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem