98-51-1Relevant articles and documents
Template-free synthesis of highly selective amorphous aluminosilicate catalyst for toluene alkylation
Peta, Sreenivasulu,Zhang, Tao,Dubovoy, Viktor,Koh, Katherine,Hu, Maocong,Wang, Xianqin,Asefa, Tewodros
, p. 155 - 159 (2018)
In this paper, we report a simple template-free synthetic method that produces amorphous, nanoporous aluminosilicate and highly selective catalyst for toluene alkylation. The structure and composition of the material and its corresponding control material are characterized by various techniques. The material shows excellent catalytic selectivity for alkylation of toluene by tert-butyl alcohol in temperatures between 50–150 °C under atmospheric pressure, producing exclusively 4-tert-butlytoluene (ca. 99%).
Using Data Science To Guide Aryl Bromide Substrate Scope Analysis in a Ni/Photoredox-Catalyzed Cross-Coupling with Acetals as Alcohol-Derived Radical Sources
Doyle, Abigail G.,Gandhi, Shivaani S.,Jiang, Shutian,Kariofillis, Stavros K.,Martinez Alvarado, Jesus I.,?urański, Andrzej M.
supporting information, p. 1045 - 1055 (2022/01/19)
Ni/photoredox catalysis has emerged as a powerful platform for C(sp2)–C(sp3) bond formation. While many of these methods typically employ aryl bromides as the C(sp2) coupling partner, a variety of aliphatic radical sources have been investigated. In principle, these reactions enable access to the same product scaffolds, but it can be hard to discern which method to employ because nonstandardized sets of aryl bromides are used in scope evaluation. Herein, we report a Ni/photoredox-catalyzed (deutero)methylation and alkylation of aryl halides where benzaldehyde di(alkyl) acetals serve as alcohol-derived radical sources. Reaction development, mechanistic studies, and late-stage derivatization of a biologically relevant aryl chloride, fenofibrate, are presented. Then, we describe the integration of data science techniques, including DFT featurization, dimensionality reduction, and hierarchical clustering, to delineate a diverse and succinct collection of aryl bromides that is representative of the chemical space of the substrate class. By superimposing scope examples from published Ni/photoredox methods on this same chemical space, we identify areas of sparse coverage and high versus low average yields, enabling comparisons between prior art and this new method. Additionally, we demonstrate that the systematically selected scope of aryl bromides can be used to quantify population-wide reactivity trends and reveal sources of possible functional group incompatibility with supervised machine learning.
A Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light
Qiu, Wenting,Shi, Shuai,Li, Ruining,Lin, Xianfeng,Rao, Liangming,Sun, Zhankui
supporting information, p. 1255 - 1258 (2021/05/05)
A visible-light-induced metal-free desulfurization method for thiols and disulfides has been explored. This radical desulfurization features mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small molecules, but also to peptides.
Flow Friedel–Crafts alkylation of 1-adamantanol with arenes using HO-SAS as an immobilized acid catalyst
Kasakado, Takayoshi,Hyodo, Mamoru,Furuta, Akihiro,Kamardine, Aina,Ryu, Ilhyong,Fukuyama, Takahide
, p. 2253 - 2257 (2020/12/15)
In this communication flow Friedel–Crafts alkylation was studied using hydroxy-substituted sulfonic acid-functionalized silica as a catalyst and 1-adamantanol as a model substrate. The reaction of 1-adamantanol (1a) with toluene (2a) proceeded well with 5 min of residence time at 120°C to give good yield of 1-tolyladamantane (3a) as a 1:9 mixture of meta and para isomers. When the flow synthesis was carried out over 2.5 hr of running time, the collected five fractions contain the product 3a in 97–92% yields, suggesting the durability of the catalyst.