146855-63-2Relevant academic research and scientific papers
Iron(II) and Copper(I) Control the Total Regioselectivity in the Hydrobromination of Alkenes
Cruz, Daniel A.,Sinka, Victoria,De Armas, Pedro,Steingruber, Hugo Sebastian,Fernández, Israel,Martín, Víctor S.,Miranda, Pedro O.,Padrón, Juan I.
, p. 6105 - 6109 (2021/08/18)
A new method that allows the complete control of the regioselectivity of the hydrobromination reaction of alkenes is described. Herein, we report a radical procedure with TMSBr and oxygen as common reagents, where the formation of the anti-Markovnikov product occurs in the presence of parts per million amounts of the Cu(I) species and the formation of the Markovnikov product occurs in the presence of 30 mol % iron(II) bromide. Density functional theory calculations combined with Fukui's radical susceptibilities support the obtained results.
Scalable and Phosphine-Free Conversion of Alcohols to Carbon-Heteroatom Bonds through the Blue Light-Promoted Iodination Reaction
Liu, Bin,Elder, W. Zachary,Miyake, Garret M.
supporting information, p. 3717 - 3727 (2020/03/04)
One of the fundamental and highly valuable transformations in organic chemistry is the nucleophilic substitution of alcohols. Traditionally, these reactions require strategies that employ stoichiometric hazardous reagents and are associated with difficulty in purification of the by-products. To overcome these challenges, here, we report a simple route toward the diverse conversion of alcohols via an SN2 pathway, in which blue light-promoted iodination is used to form alkyl iodide intermediates from simple unreactive alcohols. The scope of the process tolerates a range of nucleophiles to construct C-N, C-O, C-S, and C-C bonds. Furthermore, we also demonstrate that this method can be used for the preparation and late-stage functionalization of pharmaceuticals, as highlighted by the syntheses of thiocarlide, butoxycaine, and pramoxine.
Visible-Light Photocatalysis Employing Dye-Sensitized Semiconductor: Selective Aerobic Oxidation of Benzyl Ethers
Ren, Li,Yang, Ming-Meng,Tung, Chen-Ho,Wu, Li-Zhu,Cong, Huan
, p. 8134 - 8138 (2017/12/08)
The aerobic oxidation is an attractive approach toward environmentally benign synthesis of fine chemicals. In addition, dye-sensitized semiconductors are underdeveloped photocatalysts for selective organic synthesis. With the aid of catalytic eosin Y-sensitized titanium dioxide, we have developed efficient aerobic photooxidation of benzyl ethers to benzoates, featuring low cost, high atom economy, broad substrate scope, and user-friendly setup. Furthermore, preliminary mechanistic studies established that the reaction pathway likely entails a photoinduced, radical-based two-step process via an isolable peroxide intermediate.
Acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase
Nguyen, Corinne,Ruda, Gian Filippo,Schipani, Alessandro,Kasinathan, Ganasan,Leal, Isabel,Musso-Buendia, Alexander,Kaiser, Marcel,Brun, Reto,Ruiz-Pérez, Luis M.,Sahlberg, Britt-Louise,Johansson, Nils Gunnar,González-Pacanowska, Dolores,Gilbert, Ian H.
, p. 4183 - 4195 (2007/10/03)
We report the discovery of novel uracil-based acyclic compounds as inhibitors of deoxyuridine 5′-triphosphate nucleotidohydrolase (dUTPase), an enzyme involved in nucleotide metabolism that has been identified as a promising target for the development of
