Cheng, Chen; Hartwig, John F. published an article on February 21 ,2014. The article was titled 《Rhodium-Catalyzed Intermolecular C-H Silylation of Arenes with High Steric Regiocontrol》, and you may find the article in Science (Washington, DC, United States).Electric Literature of C14H21BO3 The information in the text is summarized as follows:
Regioselective C-H functionalization of arenes has widespread applications in synthetic chem. The regioselectivity of these reactions is often controlled by directing groups or steric hindrance ortho to a potential reaction site. Here, authors report a catalytic intermol. C-H silylation of unactivated arenes that manifests very high regioselectivity through steric effects of substituents meta to a potential site of reactivity. The silyl moiety can be further functionalized under mild conditions but is also inert toward many common organic transformations, rendering the silylarene products useful building blocks. The remote steric effect that we observe results from the steric properties of both the rhodium catalyst and the silane. In the experiment, the researchers used 2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1Electric Literature of C14H21BO3)
2-(4-Methoxy-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(cas: 214360-63-1) belongs to ethers. Ethers lack the hydroxyl groups of alcohols. Without the strongly polarized O―H bond, ether molecules cannot engage in hydrogen bonding with each other. Electric Literature of C14H21BO3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem