Li, Guolin published the artcileTransition-metal-free formal cross-coupling of aryl methyl sulfoxides and alcohols via nucleophilic activation of C-S bond, Recommanded Product: 2-Methoxynaphthalene, the publication is Nature Communications (2020), 11(1), 2890, database is CAplus and MEDLINE.
A transition-metal-free cross-coupling strategy utilizing aryl(heteroaryl) Me sulfoxides R1S(O)Me (R1 = Ph, 4-NCC6H4, 2-naphthyl, 3-pyridyl, 2-benzimidazolyl, etc.) and alcs. R2OH (R2 = Me, i-Pr, 2-cyclohexylethyl, 1-adamantylmethyl, etc.) to afford alkyl aryl(heteroaryl) ethers R1OR2 is reported. Two drug mols. were successfully prepared using this protocol as a key step and emphasized its potential utility in medicinal chem. A DFT computational study suggests that the reaction proceeds via initial addition of the alkoxide to the sulfoxide. This adduct facilitates further intramol. addition of the alkoxide to the aromatic ring wherein charge on the aromatic system is stabilized by the nearby potassium cation. Rate-determining fragmentation then delivers Me sulfenate and the aryl or heteroaryl ether. This study establishes the feasibility of nucleophilic addition to an appended sulfoxide as a means to form a bond to aryl(heteroaryl) systems and this modality is expected to find use with many other electrophiles and nucleophiles leading to new cross-coupling processes.
Nature Communications published new progress about 93-04-9. 93-04-9 belongs to ethers-buliding-blocks, auxiliary class Naphthalene,Ether, name is 2-Methoxynaphthalene, and the molecular formula is C11H10O, Recommanded Product: 2-Methoxynaphthalene.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem