Rhodium-catalyzed borylation of aryl 2-pyridyl ethers through cleavage of the carbon-oxygen bond: borylative removal of the directing group was written by Kinuta, Hirotaka;Tobisu, Mamoru;Chatani, Naoto. And the article was included in Journal of the American Chemical Society in 2015.SDS of cas: 365564-07-4 This article mentions the following:
Aryl 2-pyridyl ethers ArOPy-2 undergo rhodium-catalyzed borylative CAr-O bond activation in reaction with diboronates B2pin2 and B2neo2, giving arylboronic esters ArB(OR)2 together with 2-pyridone; the o-directing 2-pyridyl groups may be used for regioselective functionalization prior to borylation, thus accessing o-functionalized arylboronates. The straightforward synthesis of 1,2-disubstituted arenes was enabled through catalytic ortho C-H bond functionalization directed by the 2-pyridyloxy group followed by substitution of this group with a boryl group. Several control experiments revealed that the presence of a sp2 nitrogen atom at the 2-position of the substrate and the use of a boron-based reagent were crucial for the activation of the relatively inert C(aryl)-O bond of aryl 2-pyridyl ethers. In the experiment, the researchers used many compounds, for example, 2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4SDS of cas: 365564-07-4).
2-(3,5-Dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (cas: 365564-07-4) belongs to ethers. Relative to alcohols, ethers are generally less dense, are less soluble in water, and have lower boiling points. They are relatively unreactive. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).SDS of cas: 365564-07-4
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem