2933-55-3Relevant academic research and scientific papers
Aza-Matteson Reactions via Controlled Mono-and Double-Methylene Insertions into Nitrogen-Boron Bonds
Xie, Qiqiang,Dong, Guangbin
supporting information, p. 14422 - 14427 (2021/09/29)
Boron-homologation reactions represent an efficient and programmable approach to prepare alkylboronates, which are valuable and versatile synthetic intermediates. The typical boron-homologation reaction, also known as the Matteson reaction, involves formal carbenoid insertions into C-B bonds. Here we report the development of aza-Matteson reactions via carbenoid insertions into the N-B bonds of aminoboranes. By changing the leaving groups of the carbenoids and altering Lewis acid activators, selective mono- and double-methylene insertions can be realized to access various α- and β-boron-substituted tertiary amines, respectively, from common secondary amines. The derivatization of complex amine-containing bioactive molecules, diverse functionalization of the boronate products, and sequential insertions of different carbenoids have also been achieved.
Ru-Catalyzed Switchable N-Hydroxyethylation and N-Acetonylation with Crude Glycerol
Xin, Zhuo,Jia, Le,Huang, Yuxing,Du, Chen-Xia,Li, Yuehui
, p. 2007 - 2011 (2020/03/19)
Highly efficient Ru-catalyzed selective C?C or C?O bond cleavage of polyols (e.g., crude glycerol) for N-hydroxyethylation or N-acetonylation of amines was achieved through the hydrogen-borrowing approach. A variety of amines were transformed to the desired amino alcohols/ketones in moderate-to-excellent yields, opening up new avenues for generation of oxygenated pharmaceuticals and fine chemicals from renewable raw materials. The use of new redox-active catalysts containing bisphosphine/thienylmethylamine ligands allows this hydrogen-borrowing system to be operated selectively under both basic and acidic conditions.
Direct hydroxyethylation of amines by carbohydrates: Via ruthenium catalysis
Jia, Le,Makha, Mohamed,Du, Chen-Xia,Quan, Zheng-Jun,Wang, Xi-Cun,Li, Yuehui
supporting information, p. 3127 - 3132 (2019/06/18)
An efficient and halogen-free catalytic methodology for the synthesis of β-amino alcohols from aromatic amines and biomass-derived carbohydrates is demonstrated for the first time. The activation of C5/C6 sugars by a ruthenium catalyst selectively generates the C2 alkylating reagent glycolaldehyde. The transformation involves metal-catalyzed hydrogen borrowing for the reduction of the imine intermediate. A series of arylamines bearing various substituents were successfully transformed into the desired products in good to excellent yields.
Synthetic technology of hydroxyethylaniline ester (III)
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Paragraph 0042; 0043; 0056; 0057; 0062, (2016/11/02)
The invention discloses a synthetic technology of hydroxyethylaniline ester (III). The synthesis process is shown by a chemical equation shown in the description. The technology has the following advantages: 1, the advantage of few instant reaction substances of a micro-channel reactor is used, so the flammable and explosive disadvantages of a hydroxyethylation reaction in a routine kettle are solved, the process safety is increased, and current chemical engineering safety operation requirements are met; and 2, the advantage of high mixing efficiency of the micro-channel reactor is used, the reaction can be carried out under solvent-free conditions when a hydroxyethylation reaction raw material is liquid, and when the excess amount of ethylene oxide is very small, so a reaction solution obtained after the hydroxyethylation reaction ends can be esterified in the micro-channel reactor, serial operation of two-step reactions is realized, and manpower and three wastes are greatly reduced. The technology is a new technology with simplified processes, and accords with environmental protection and safety requirements.
