261376-67-4Relevant academic research and scientific papers
An economic and practical synthesis of the 2-tetrahydrofuranyl ether protective group
Falck,Li, De Run,Bejot, Romain,Mioskowski, Charles
, p. 5111 - 5113 (2006)
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.
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.
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.
Environmentally friendly tetrahydrofuranylation of alcohols using NaHSO4SiO2 under solvent-free conditions
Kinfe, Henok H.,Terblanche, Sullivan,Tshivhase, Konanani D.,Ravhura, Livhuwani
experimental part, p. 272 - 273 (2012/05/20)
A simple, environmentally friendly, and efficient tetrahydrofuranylation of alcohols has been developed using NaHSO4SiO2 (0.5 mol%) as a catalyst under solvent-free conditions to yield corresponding THF ethers in good to excellent yi
Vanadium(III) chloride (VCl3): Efficient reagent for the introduction of tetrahydrofuran-based acetal protecting groups for alcohols
Das, Biswanath,Krishnaiah, Maddeboina,Reddy, Vtukuri Saidi,Laxminarayana, Keetha
, p. 2163 - 2166 (2008/03/18)
Treatment of different types of alcohols with tetrahydrofuran (THF) in the presence of VCl3 and CCl4 smoothly afforded the corresponding THF-based acetals in excellent yields. The reaction is fast at room temperature, and several functional groups are tolerated, with no racemization being observed. A radical mechanism, based on Cl3C ? as the active species, is proposed for this novel kind of transformation, which complements the classical tetrahydro-2H-pyran-2-yl (THP) protocol.
Acetonyltriphenylphosphonium bromide and its polymer-supported analogues as catalysts in protection and deprotection of alcohols as alkyl vinyl ethers
Hon, Yung-Son,Lee, Chia-Fu,Chen, Rong-Jiunn,Szu, Ping-Hui
, p. 5991 - 6001 (2007/10/03)
Both acetonyltriphenylphosphonium bromide (ATPB, 1) and poly-p-styryldiphenylacetonylphosphonium bromide (A) were effective catalysts in the protection of alcohols as THP, THF, and EE ethers as well as the cleavage of THP, THF, and EE ethers to the corresponding alcohols. They could be applied to 1°, 2° and 3° alcohols, phenol and acid-labile alcohols. Both ATPB and catalyst A are excellent catalysts in the present study. It needed only 1×10-2-1.25×10-2 mol equiv. of the polymer-supported catalyst A in the reactions.
Acetonyltriphenylphosphonium bromide in organic synthesis: An extremely efficient catalyst for the protection and deprotection of alcohols as alkyl vinyl ethers
Hon, Yung-Son,Lee, Chia-Fu
, p. 2389 - 2392 (2007/10/03)
Acetonyltriphenylphosphonium bromide (ATPB) was an extremely effective catalyst in the preparation of THP, THF, and EE ethers as well as cleavage of THP, THF, and EE ethers to the corresponding alcohols. It could be applied to 1°, 2°and 3°alcohols and phenol.
