68299-58-1Relevant academic research and scientific papers
Mechanochemical Nucleophilic Substitution of Alcohols via Isouronium Intermediates**
Dalidovich, Tatsiana,Nallaparaju, Jagadeesh Varma,Shalima, Tatsiana,Aav, Riina,Kananovich, Dzmitry G.
, (2022/01/26)
An expansion of the solvent-free synthetic toolbox is essential for advances in the sustainable chemical industry. Mechanochemical reactions offer a superior safety profile and reduced amount of waste compared to conventional solvent-based synthesis. Here
Palladium-catalyzed substitution and cross-coupling of benzylic fluorides
Blessley, George,Holden, Patrick,Walker, Matthew,Brown, John M.,Gouverneur, Veronique
supporting information; experimental part, p. 2754 - 2757 (2012/07/16)
Benzylic fluorides are suitable substrates for Pd(0)-catalyzed Tsuji-Trost substitution using carbon, nitrogen, oxygen, and sulfur nucleophiles and for cross-coupling with phenylboronic acid. For the bifunctional substrate 4-chlorobenzyl fluoride, fine-tuning of the reaction conditions allows for the regioselective displacement of either the chlorine or fluorine substituent. The leaving group ability of fluoride vs other groups displaced in substitution is CF3CO2 ≈ p-NO2C6H 4CO2 ≈ OCO2CH3 > F > CH3CO2, a ranking similar to allylic fluorides under Pd catalysis.
Direct benzylic alkylation via Ni-catalyzed selective benzylic sp 3 C-O activation
Guan, Bing-Tao,Xiang, Shi-Kai,Wang, Bi-Qin,Sun, Zuo-Peng,Wang, Yang,Zhao, Ke-Qing,Shi, Zhang-Jie
, p. 3268 - 3269 (2008/10/09)
This article demonstrates the first cross coupling of benzyl ether with Grignard reagents via Ni-catalyzed benzylic sp3 C-O activation with high efficiency and excellent chemoselectivity. Benzylic sp3 C-O and aryl sp2 C-O were differentiated, controlled by ligands. Copyright
Fragmentation of anion radicals with elimination of aryloxy groups
Dneprovskii,Fedosov
, p. 1438 - 1443 (2007/10/03)
4-Vinylbenzyl phenyl ether, 4-phenylbenzyl phenyl ether, 1- and 2-naphthylmethyl phenyl ethers react with sodium thiophenolate under photochemical stimulation with replacement of the phenoxy group. The composition of reaction products and relation of reactivity to the structure of substrates is consistent with anion-radical mechanism. The corresponding methoxy and cyano derivatives do not undergo the reaction.
Synthesis of aromatic ethers without organic solvent and inorganic carrier under microwave irradiation
Wang, Jin-Xian,Zhang, Manli,Xing, Zhiliang,Hu, Yulai
, p. 301 - 305 (2007/10/03)
A simple, rapid and efficient procedure for the synthesis of aromatic ethers via microwave irradiation without any organic solvent and inorganic carrier is reported.
Electron Apportionment in Cleavage of Radical Anions. 2. Naphthylmethyl Phenyl Ethers vs. Naphthyl Benzyl Ethers
Maslak, Przemyslaw,Guthrie, Robert D.
, p. 2637 - 2640 (2007/10/02)
Naphthylmethyl phenyl ethers and naphthyl benzyl ethers were found to undergo scission of the H2C-O bond when treated with radical anions of anthracene or fluoranthene.Under comparable conditions, ethers of the naphthylmethyl phenyl series (α and β) reacted more than 10E4 times faster than ethers of the naphthyl benzyl series (α and β).This preference for regioconservation of spin density in the scission process is interpreted in terms of ?-bond polarization at the transition state.
