151252-07-2Relevant academic research and scientific papers
Direct Facile Tetrahydrofuranylation Of Alcohols Through Radical Coupling With (Bu4N)2S2O8
Jung, Jae Chul,Choi, Hyun Chul,Kim, Yong Hae
, p. 3581 - 3584 (1993)
Primary, secondary and tertiary alcohols can be converted in excellent yields into their 2-tetrahydrofuranyl-ethers in the presence of n-tetrabutylammonium peroxydisulfate under nearly neutral condition in tetrahydrofuran.
Tetrahydrofuranylation of alcohols catalyzed by alkylperoxy- λ3-iodane and carbon tetrachloride
Ochiai, Masahito,Sueda, Takuya
, p. 3557 - 3559 (2004)
Reaction of primary and secondary alcohols with tetrahydrofuran and a catalytic amount of 1-tert-butylperoxy-1,2-benziodoxol-3(1H)-one in the presence of carbon tetrachloride at 50°C provides an efficient method for protecting the hydroxy group as 2-tetrahydrofuranyl ethers.
Visible Light-Induced α-C(sp3)-H Acetalization of Saturated Heterocycles Catalyzed by a Dimeric Gold Complex
Si, Xiaojia,Zhang, Lumin,Wu, Zuozuo,Rudolph, Matthias,Asiri, Abdullah M.,Hashmi, A. Stephen K.
supporting information, p. 5844 - 5849 (2020/08/12)
Saturated heterocyclic acetals are useful fragments in organic synthesis and other fields. Herein, C(sp3)-H dehydrogenative cross-couplings of ethers, tetrahydrothiophenes, and pyrrolidines were achieved under visible light irradiation by using iodobenzene and an in situ-formed gold complex. The broad functional group compatibility and substrate scope indicate that our strategy is a promising way to synthesize acetal analogues. The method was successfully applied in late-stage modifications of bioactive molecules. Gram scale syntheses and mechanistic studies are also presented.
An economic and practical synthesis of the 2-tetrahydrofuranyl ether protective group
Falck,Li, De Run,Bejot, Romain,Mioskowski, Charles
, p. 5111 - 5113 (2007/10/03)
Primary, secondary, and tertiary alcohols as well as phenols and carbohydrates are efficiently transformed into the corresponding 2-tetrahydrofuranyl ethers by a combination of Mn(0) powder and CCl4 in tetrahydrofuran.
Use of allyl, 2-tetrahydrofuryl, and 2-tetrahydropyranyl ethers as useful C3-, C4-, and C5-carbon sources: Palladium-catalyzed allylation of aldehydes
Shimizu, Masamichi,Kimura, Masanari,Tamaru, Yoshinao
, p. 6629 - 6642 (2007/10/03)
Palladium-diethylzinc or palladium-triethylborane catalytically promotes self-allylation of 2-(allyloxy)tetrahydrofurans, 2-(allyloxy)tetrahydropyrans, and their hydroxy derivatives on the rings (ribose, glucose, mannose, deoxyribose, deoxyglucose). All the reactions proceed at room temperature and provide polyhydroxyl products, sharing a structural motif of a homoallyl alcohol, in good to excellent yields with high levels of stereoselectivity. Useful Crunit elongation, which makes the best use of an allyl ether as a protecting group and a nucleophilic allylation agent, is demonstrated. Mechanisms for the umpolung reaction (of an allyl ether into an allylic anion) and stereoselectivity associated with allylation of aldehydes are discussed.
