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Search Results (3)

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Keywords = N-arylhydroxylamine

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17 pages, 5811 KiB  
Article
An Efficient Continuous Flow Synthesis for the Preparation of N-Arylhydroxylamines: Via a DMAP-Mediated Hydrogenation Process
by Jianli Chen, Xinyu Lin, Feng Xu, Kejie Chai, Minna Ren, Zhiqun Yu, Weike Su and Fengfan Liu
Molecules 2023, 28(7), 2968; https://doi.org/10.3390/molecules28072968 - 27 Mar 2023
Cited by 6 | Viewed by 3427
Abstract
The selective hydrogenation of nitroarenes to N-arylhydroxylamines is an important synthetic process in the chemical industry. It is commonly accomplished by using heterogeneous catalytic systems that contain inhibitors, such as DMSO. Herein, DMAP has been identified as a unique additive for increasing [...] Read more.
The selective hydrogenation of nitroarenes to N-arylhydroxylamines is an important synthetic process in the chemical industry. It is commonly accomplished by using heterogeneous catalytic systems that contain inhibitors, such as DMSO. Herein, DMAP has been identified as a unique additive for increasing hydrogenation activity and product selectivity (up to >99%) under mild conditions in the Pt/C-catalyzed process. Continuous-flow technology has been explored as an efficient approach toward achieving the selective hydrogenation of nitroarenes to N-arylhydroxylamines. The present flow protocol was applied for a vast substrate scope and was found to be compatible with a wide range of functional groups, such as electron-donating groups, carbonyl, and various halogens. Further studies were attempted to show that the improvement in the catalytic activity and selectivity benefited from the dual functions of DMAP; namely, the heterolytic H2 cleavage and competitive adsorption. Full article
(This article belongs to the Section Applied Chemistry)
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14 pages, 2685 KiB  
Article
Copper-Catalyzed Synthesis of Axially Chiral Biaryls with Diaryliodonium Salts as Arylation Reagents
by Ji-Wei Zhang, Shao-Hua Xiang, Shaoyu Li and Bin Tan
Molecules 2021, 26(11), 3223; https://doi.org/10.3390/molecules26113223 - 27 May 2021
Cited by 6 | Viewed by 3962
Abstract
NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [...] Read more.
NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation of N-arylhydroxylamines or N-arylhydrazines with diaryliodonium salts and [3,3]-sigmatropic rearrangement. This reaction features mild conditions, good substrate compatibility, and excellent efficiency. The practicality of this protocol was further extended by the synthesis of biaryl amino alcohols. Full article
(This article belongs to the Special Issue Synthesis, Stereochemistry and Applications of Axially Chiral Organic Molecules)
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16 pages, 1483 KiB  
Article
A General and Scalable Synthesis of Polysubstituted Indoles
by David Tejedor, Raquel Diana-Rivero and Fernando García-Tellado
Molecules 2020, 25(23), 5595; https://doi.org/10.3390/molecules25235595 - 28 Nov 2020
Cited by 4 | Viewed by 4548
Abstract
A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and [...] Read more.
A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies. Full article
(This article belongs to the Collection Heterocyclic Compounds)
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