1918-61-2Relevant articles and documents
Tetrahydrofuranylation of alcohols using hypervalent iodine reagents
French, Andrew N.,Cole, Jonathan,Wirth, Thomas
, p. 2291 - 2294 (2004)
Alcohols are converted to their corresponding 2-tetrahydrofuranyl ethers using (diacetoxyiodo)benzene in THF. Reactions are carried out under reflux, or, more effectively, under microwave irradiation. Yields up to 81% are reported without the use of chlorinated solvents.
Metal-free tetrahydrofuranylation of alcohols with tertbutyl nitrite
Bi, Kang,Cai, Yue-Ming,Lin, Junyue,Liu, Miao-Chang,Zhou, Yun-Bing
supporting information, (2020/08/06)
Metal-free tetrahydrofuranylation of alcohols in the presence of tertbutyl nitrite is described, providing a facile and green route for the protection of hydroxy groups. Mechanistic studies demonstrate that this transformation proceeds in a radical way, and involves alkyl nitrite of corresponding alcohol as the key intermediate.
Amberlyst-15-catalyzed one-pot synthesis of 2-aryltetrahydrofurans from tetrahydrofuran
Gunduz, Hande,Kumbaraci, Volkan,Talinli, Naciye
supporting information, p. 2473 - 2476,4 (2012/12/13)
A simple one-step route for the conversion of naphthols and phenols with tetrahydrofuran into corresponding 2-aryltetrahydrofurans using Amberlyst-15 as a catalyst is reported. This is the first example of the acid-mediated formation and rearrangement reactions of tetrahydrofuranyl ethers prepared from the tetrahydrofuran and aromatic/aliphatic hydroxy compounds.
An economic and efficient tetrahydrofuranylation of alcohols, imines and alkynes
Troisi, Luigino,Granito, Catia,Ronzini, Ludovico,Rosato, Francesca,Videtta, Valeria
experimental part, p. 5980 - 5983 (2010/11/21)
The tetrahydrofuranyl radical, generated by heating tetrahydrofuran in the presence of air and allyl or benzyl chloride, becomes a useful tool in order to transform the hydroxyl functions into ethers, or the CN double bond into amine, or the C-C triple bond into vinyl derivatives. A radical mechanism is proposed followed by a nucleophilic substitution for the alcohol substrate and a radical addition for the iminic and the acetylenic reactants.