100885-83-4Relevant academic research and scientific papers
Convenient Access to meta-Substituted Phenols by Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling and Oxidation
Wang, Zi,Orellana, Arturo
, p. 11445 - 11449 (2017)
We report a new approach to the synthesis of meta-substituted phenols in which a single palladium catalyst accomplishes a Suzuki–Miyaura cross-coupling between a β-chlorocyclohexenone and an arylboronic acid, and oxidation of the resulting cyclohexenone to the corresponding phenol upon introduction of a terminal oxidant and electron transfer mediator. Notably, this method also allows ready access to ortho, meta-disubstituted phenols, sterically congested biaryl phenols, and more highly substituted phenols.
Synthesis of a series of cyclic 2,4-dienones and evaluation of their Diels–Alder reactivity with maleic anhydride
Abaee, M. Saeed,Mohammadi, Mohaddeseh,Mojtahedi, Mohammad M.,Notash, Behrouz,Pirouz, Maryam
, (2022/01/11)
Diels–Alder reactions of conjugated cyclic 2,4-dienones are a versatile tool for rapid and selective synthesis of multicyclic products. A new series of these dienes were synthesized in moderate yields for the first time, by using an aqueous NaOH solution within 2–3?h time periods. Then, the diene products were evaluated for their Diels–Alder reactivity under conventional thermal conditions. Cycloaddition of the parent diene with maleic anhydride, as an standard dienophile, solely produced a single phenyl substituted endo adduct of the hexahydronaphthofuran-trione structure. The optimum conditions were then successfully used for the synthesis of other derivatives of the target structure (within 10–16?h reflux in toluene). Spectroscopic studies, including 1H NMR and 13C NMR analyses, elucidated the structure and the endo stereochemistry of the products, in which the double bond has moved to the more stable endocyclic position. In addition, X-ray crystalography of one of the derivatives approved the suggested structure.
