1416975-71-7Relevant academic research and scientific papers
Heat-or light-induced acylarylation of unactivated alkenes towards 3-(α-acyl) indolines
Dong, Ying,Fu, Tingfeng,Han, Yinghui,Li, Yanni,Liang, Deqiang,Lin, Liqing,Long, Xianhao,Yang, Ruihan,Ying, Fengyuan
, p. 5660 - 5665 (2020)
A heat-or photoredox/iron dual catalysis-enabled dehydrogenative acylarylation of N-allyl anilines leading to 2-substituted 3-(α-acyl) indolines with a quaternary stereogenic center is presented, with unactivated alkenic bonds as radical acceptors and simple aldehydes as radical precursors. This reaction features high yields, a broad substrate scope, and a great exo selectivity, and gram-scale syntheses could be readily carried out.
N-Doped Yellow TiO2 Hollow Sphere-Mediated Visible-Light-Driven Efficient Esterification of Alcohol and N-Hydroxyimides to Active Esters
Singha, Krishnadipti,Ghosh, Subhash Ch.,Panda, Asit Baran
, p. 3205 - 3212 (2019)
Herein we report a simple synthetic protocol for N-doped yellow TiO2 (N-TiO2) hollow spheres as an efficient visible-light-active photocatalyst using aqueous titanium peroxocarbonate complex (TPCC) solution as precursor and NH4OH. In the developed strategy, the ammonium ion of TPCC and NH4OH acts as nitrogen source and structure-directing agent. The synthesized N-TiO2 hollow spheres are capable of promoting the synthesis of active esters of N-hydroxyimide and alcohol through simultaneous selective oxidation of alcohol to aldehyde followed by cross-dehydrogenative coupling (CDC) under ambient conditions upon irradiation of visible light. It is possible to develop a novel and cost-effective one-pot strategy for the synthesis of important esters and amides on gram scale using the developed strategy. The catalytic activity of N-TiO2 hollow spheres is much superior to that of other reported N-TiO2 samples as well as TiO2 with varying morphology.
Synthesis of difluoromethylselenoesters from aldehydes: Via a radical process
Guo, Rui-Li,Zhu, Xue-Qing,Zhang, Xing-Long,Wang, Yong-Qiang
, p. 8976 - 8979 (2020)
Difluoromethylselenoester compounds, another important kind of organoselenium compounds, are reported herein for the first time. They can be efficiently synthesized from aldehydes and BnSeCF2H. The synthetic method features mild reaction conditions, broad substrate scope, good tolerance of functional groups, and importantly, no metal is involved in the reaction.
Synthesis of trifluoromethylthioesters from aldehydes: Via a visible light-promoted radical process
Guo, Rui-Li,Jia, Qiong,Wang, Meng-Yue,Wang, Yong-Qiang,Zhang, Xing-Long,Zhu, Xue-Qing
, p. 5918 - 5926 (2020)
We report herein an efficient, economical, and scalable trifluoromethylthiolation of aldehydes to generate trifluoromethylthioesters via a visible light-promoted radical process. The transformation features cheap reagents, simple operation, a broad substrate scope, and especially no metal involved in the reaction. Trifluoromethylthiolations of several complex aldehyde-containing bioactive compounds have been realized; thus the approach has the potential to be an important tool for the late-stage functionalization of advanced synthetic intermediates and bioactive molecules, and should have many applications in medicinal chemistry. This journal is
Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions
Ambala, Srinivas,Arvidsson, Per I.,Govender, Thavendran,Kruger, Hendrik G.,Naicker, Tricia,Rajbongshi, Kamal K.
, p. 1279 - 1286 (2020/04/15)
An efficient catalyst-free radical cross-coupling reaction between aromatic aldehydes and sulfoximines was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines in moderate to excellent yields (27 examples). This protocol proved to be rapid, easy to handle, and applicable to a broad scope of substrates.
Mechanistic investigation of the oxidation of hydrazides: Implications for the activation of the TB drug isoniazid
Amos, Ruth I. J.,Gourlay, Brendon S.,Yates, Brian F.,Schiesser, Carl H.,Lewis, Trevor W.,Smith, Jason A.
, p. 170 - 176 (2013/02/23)
Aryl hydrazides are oxidised to acyl radicals through a mechanism involving diimide intermediates that are prone to nucleophilic acyl substitution. This oxidation occurs regardless of the oxidant involved, however there is no evidence that the acyl radical formed undergoes further oxidation to the corresponding acylium ion, even in the presence of strong oxidants. This study may provide insight into the mechanism of isoniazid resistance in Mycobacterium tuberculosis. The Royal Society of Chemistry.
Synthesis of imides by palladium-catalyzed C-H functionalization of aldehydes with secondary amides
Bian, Yong-Jun,Chen, Chao-Yue,Huang, Zhi-Zhen
supporting information, p. 1129 - 1133 (2013/02/23)
An efficient palladium-catalyzed C-H functionalization of aldehydes with various N-substituted N-heteroarene-2-carboxamides has been developed for the synthesis of secondary imides. The reaction tolerates various functionalities, such as methoxy, fluoro, chloro, and bromo groups. A tentative radical mechanism for a PdII/PdIV catalytic cycle is proposed. Copyright
Organocatalytic amidation and esterification of aldehydes with activating reagents by a cross-coupling strategy
Tan, Bin,Toda, Narihiro,Barbas III, Carlos F.
supporting information, p. 12538 - 12541 (2013/02/22)
Formation on demand: An organocatalytic cross-coupling reaction of aldehydes with N-hydroxyimides, hexafluoroisopropyl alcohol, and sulfonimides has been developed. The resulting active intermediates can be directly converted into amides or esters in one pot. This simple method makes use of readily available starting materials, and the newly discovered activating reagents should find broad application in the synthesis of amides and esters. Copyright
