3355-05-3Relevant articles and documents
The radical hydroxylation of tetralol-(6) with Fenton's reagent
Hecker,Nowoczek
, p. 153 - 160 (1966)
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Regioselective and Chemoselective Reduction of Naphthols Using Hydrosilane in Methanol: Synthesis of the 5,6,7,8-Tetrahydronaphthol Core
He, Yuan,Tang, Jinghua,Luo, Meiming,Zeng, Xiaoming
supporting information, p. 4159 - 4163 (2018/07/29)
A regioselective and chemoselective method for catalytic synthesis of biologically interesting 5,6,7,8-tetrahydronaphthols by reduction of naphthols was described. The side aromatic hydrocarbons in naphthols were site-selectively reduced, using hydrosilanes in methanol, allowing for retaining functional phenol scaffolds intact. It presents a rare example of using low-cost and air-stable hydrosilane for catalytic reduction of unactivated aromatic hydrocarbons under mild conditions. This reaction is scalable and proceeds in high selectivity without the formation of 1,2,3,4-tetrahydronaphthol byproducts with toleration of sensitive functionalities such as bromide, chloride, fluoride, ketone, ester, and amide.
Synthesis of catechols from phenols via Pd-catalyzed silanol-directed C-H oxygenation
Huang, Chunhui,Ghavtadze, Nugzar,Chattopadhyay, Buddhadeb,Gevorgyan, Vladimir
supporting information; experimental part, p. 17630 - 17633 (2011/12/16)
A silanol-directed, Pd-catalyzed C-H oxygenation of phenols into catechols is presented. This method is highly site selective and general, as it allows for oxygenation of not only electron-neutral but also electron-poor phenols. This method operates via a silanol-directed acetoxylation, followed by a subsequent acid-catalyzed cyclization reaction into a cyclic silicon-protected catechol. A routine desilylation of the silacyle with TBAF uncovers the catechol product.
