51706-34-4Relevant academic research and scientific papers
Anhydrous FePO4 as a cost-effective and recyclable catalyst for tetrahydropyranylation and tetrahydrofuranylation of alcohols and phenols
Behbahani, Farahnaz K.,Farahani, Mona
experimental part, p. 431 - 435 (2012/04/17)
In this article, a mild and efficient protocol for the tetrahydropyranylation and tetrahydrofuranylation of various aliphatic and benzylic alcohols and phenols into their corresponding THP and THF ethers (with 3,4-dihydro- 2H-pyran, DHP and 2,3-dihydrofuran, DHF) has been developed using a catalytic amount of anhydrous FePO4 at room temperature and relatively short reaction times in good to excellent yields.
Generally applicable organocatalytic tetrahydropyranylation of hydroxy functionalities with very low catalyst loading
Kotke, Mike,Schreiner, Peter R.
, p. 779 - 790 (2008/01/03)
This paper presents the first acid-free, organocatalytic tetrahydropyran and 2-methoxypropene protection of alcohols, phenols, and other ROH derivatives utilizing privileged N,N′-bis[3,5-bis(trifluoromethyl)phenyl]thiourea and a polystyrene-bound analogue. The reactions are broadly applicably (also on preparative scale), in particular, to acid-sensitive substrates such as aldol products, hydroxy esters, acetals, silyl-protected alcohols, and cyanohydrins. The catalytic efficiency is truly remarkably with turnover numbers of 100,000 and turnover frequencies of up to 5700 h-1 at catalyst loadings down to 0.001 mol%. The computationally supported mechanistic interpretation emphasizes the hydrogen bond assisted heterolysis of the alcohol and concomitant preferential stabilization of the oxyanion hole in the transition state. Georg Thieme Verlag Stuttgart.
Silylation and tetrahydropyranylation of alcohols catalyzed by Al(HSO 4)3
Shirini, Farhad,Zolfigol, Mohammad Ali,Abedini, Masoumeh
, p. 1982 - 1985 (2007/10/03)
Trimethylsilylation and tetrahydropyranylation of alcohols are efficiently catalyzed by Al(HSO4)3. All reactions were performed under mild and completely heterogeneous conditions in good-to-high yields.
Potassium dodecatangestocobaltate trihydrate (K5CoW12O40·3H2O): A mild and efficient catalyst for the tetrahydropyranylation of alcohols and their detetrahydropyranylation
Habibi, Mohammad H.,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Mirkhani, Valiollah,Yadollahi, Bahram
, p. 2851 - 2853 (2007/10/03)
A simple, mild and effective method for tetrahydropyranylation of a variety of alcohols and cleavage of their tetrahydropyranyl ethers at ambient temperature in the presence of K5CoW12O40·3H2O as the catalyst with high turnovers is described.
