Aerobic oxidative coupling of alcohols and amines over Au–Pd/resin in water: Au/Pd molar ratios switch the reaction pathways to amides or imines

Literature Information

Publication Date 2013-08-06
DOI 10.1039/C3GC41117F
Impact Factor 10.182
Authors

Wentao Wang, Aiqin Wang, Yitao Cui, Xiaofeng Yang, Yanqiang Huang, Xiaoyan Liu, Wengang Liu, Jin-Young Son, Hiroshi Oji, Tao Zhang


View Original

Abstract

A facile switch of the reaction pathways of aerobic oxidative coupling of alcohols and amines from amidation to imination was realized for the first time by tuning the Au/Pd ratios in ion-exchange resin supported Au–Pd alloy catalysts (Au–Pd/resin). Amides were obtained with high yields on Au6Pd/resin while imines were obtained over AuPd4/resin. Various alcohols and amines underwent oxidative coupling smoothly in water to afford the desired products with good to excellent yields. Further investigation on the reaction mechanism suggested the synergistic effect between Au and Pd determined the adsorption strength of the aldehyde intermediate, which in turn dictated the reaction pathways. That is, on Au-rich alloys (e.g., Au6Pd) absorbed aldehyde species was formed, followed by further oxidation to yield amides, while on Pd-rich alloys (e.g., AuPd4), free aldehyde was generated, which then underwent condensation with amines to produce imines. The discovery might provide avenues to develop new efficient catalysts for the green synthesis of special chemicals.

Related Literature

Enhanced fluorescent resonant energy transfer of DNA conjugates complexed with surfactants and divalent metal ions

Taeseok Oh, Jae-Young Choi

2016-03-08 Communication

DOI: 10.1039/C5AN02516H

Efficient enantiorecognition of amino acids under a stimuli-responsive system: synthesis, characterization and application of electroactive rotaxane

Datong Wu, Fei Pan, Gao-Chao Fan, Ziming Zhu, Li Gao, Yongxin Tao, Yong Kong

2019-09-23 Paper

DOI: 10.1039/C9AN01692A

A colorimetric and fluorescent dual probe for palladium in aqueous medium and live cell imaging

Jin-wu Yan, Xiao-lin Wang, Qi-feng Tan, Pei-fen Yao, Jia-heng Tan, Lei Zhang

2016-03-11 Communication

DOI: 10.1039/C6AN00204H

Determination of catecholamines and related compounds in mouse urine using column-switching HPLC

Takahiro Kanamori, Takashi Funatsu, Makoto Tsunoda

2016-03-31 Paper

DOI: 10.1039/C5AN02617B

Discriminative potential of ion mobility spectrometry for the detection of fentanyl and fentanyl analogues relative to confounding environmental interferents‡

Thomas P. Forbes, Jeffrey Lawrence, Jennifer R. Verkouteren, R. Michael Verkouteren

2019-09-27 Paper

DOI: 10.1039/C9AN01771B

A near-infrared fluorescent aza-bodipy probe for dual-wavelength detection of hydrogen peroxide in living cells

Jingjing Xu, Jingying Zhai, Yanmei Xu, Jingwei Zhu, Yu Qin, Dechen Jiang

2016-03-11 Communication

DOI: 10.1039/C6AN00262E

Exosome-specific tumor diagnosis via biomedical analysis of exosome-containing microRNA biomarkers

Jun Yu, Jingyan Lin, Ying Liu

2019-08-21 Paper

DOI: 10.1039/C9AN00777F

Front cover

Cover

DOI: 10.1039/C9AN90095K

Correction: Bacterial detection and identification from human synovial fluids on an integrated microfluidic system

Ting-Hang Liu, Shu-Shen Cheng, Huey-Ling You, Mel S. Lee

2019-09-11 Correction

DOI: 10.1039/C9AN90087J

You might also like

155412-88-71-(3-Aminophenyl)-3-...
Compound Q&A

How should waste containing 1-(D-Ribofuranosyl)-1,4-dihydro-3-pyridinecarboxamide (CAS: 19132-12-8) be handled?

Waste containing 1-(D-Ribofuranosyl)-1,4-dihydro-3-pyridinecarboxamide (CAS: 191...

19132-12-81-(D-Ribofuranosyl)-...
Compound Q&A

What regulatory guidelines apply to 2-Methyl-2-propanyl 3-bromo-3-(hydroxymethyl)-1-azetidinecarboxylate (CAS: 2007919-81-3)?

2-Methyl-2-propanyl 3-bromo-3-(hydroxymethyl)-1-azetidinecarboxylate (CAS: 20079...

2007919-81-32-Methyl-2-propanyl ...
Compound Q&A

What is N-(4-Chloro-2-pyridinyl)acetamide (CAS: 245056-66-0)?

N-(4-Chloro-2-pyridinyl)acetamide (CAS: 245056-66-0) is a chemical compound with...

245056-66-0N-(4-Chloro-2-pyridi...
Compound Q&A

What is 5-Chloro-2-hydroxybenzoic acid (CAS: 321-14-2)?

5-Chloro-2-hydroxybenzoic acid, also known as 5-chlorosalicylic acid, is an arom...

321-14-25-Chloro-2-hydroxybe...
Compound Q&A

What precautions should be taken when handling 1,1-Dichloro-1-fluoroethane (CAS: 1717-00-6)?

When handling 1,1-Dichloro-1-fluoroethane (CAS: 1717-00-6), it is important to u...

1717-00-61,1-Dichloro-1-fluor...
Compound Q&A

What are the physical and chemical properties of Fmoc-(2S,3R)-3-phenylpyrrolidine-2-carboxylic acid (CAS: 281655-32-1)?

Fmoc-(2S,3R)-3-phenylpyrrolidine-2-carboxylic acid is a white crystalline solid ...

281655-32-1Fmoc-(2S,3R)-3-pheny...
Compound Q&A

What are the main uses of 4-Amino-5-bromo-2-pyridinecarboxylic acid (CAS: 1363381-01-4)?

4-Amino-5-bromo-2-pyridinecarboxylic acid is primarily used as a precursor in th...

1363381-01-44-Amino-5-bromo-2-py...
1007881-98-2(S)-tert-butyl 2-((2...
Compound Q&A

What precautions should be taken when handling 8-bromo-2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-one (CAS: 688363-73-7)?

When handling 8-bromo-2,2-dimethyl-3,4-dihydro-2H-1,4-benzoxazin-3-one, use prop...

688363-73-78-bromo-2,2-dimethyl...

Source Journal

Green Chemistry

Green Chemistry
CiteScore: 16.1
Self-citation Rate: 7.5%
Articles per Year: 944

Green Chemistry provides a unique forum for the publication of innovative research on the development of alternative green and sustainable technologies. The scope of Green Chemistry is based on, but not limited to, the definition proposed by Anastas and Warner (Green Chemistry: Theory and Practice, P T Anastas and J C Warner, Oxford University Press, Oxford, 1998). Green chemistry is the utilisation of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products. Green Chemistry is at the frontiers of this continuously-evolving interdisciplinary science and publishes research that attempts to reduce the environmental impact of the chemical enterprise by developing a technology base that is inherently non-toxic to living things and the environment. Submissions on all aspects of research relating to the endeavour are welcome. The journal publishes original and significant cutting-edge research that is likely to be of wide general appeal. To be published, work must present a significant advance in green chemistry. Papers must contain a comparison with existing methods and demonstrate advantages over those methods before publication can be considered. For more information please see this Editorial. Coverage includes the following, but is not limited to: Design (e.g. biomimicry, design for degradation/recycling/reduced toxicity…) Reagents & Feedstocks (e.g. renewables, CO2, solvents, auxiliary agents, waste utilization…) Synthesis (e.g. organic, inorganic, synthetic biology…) Catalysis (e.g. homogeneous, heterogeneous, enzyme, whole cell…) Process (e.g. process design, intensification, separations, recycling, efficiency…) Energy (e.g. renewable energy, fuels, photovoltaics, fuel cells, energy storage, energy carriers…) Applications (e.g. electronics, dyes, consumer products, coatings, pharmaceuticals, preservatives, building materials, chemicals for industry/agriculture/mining…) Impact (e.g. safety, metrics, LCA, sustainability, (eco)toxicology…) Green chemistry is, by definition, a continuously-evolving frontier. Therefore, the inclusion of a particular material or technology does not, of itself, guarantee that a paper is suitable for the journal. To be suitable, the novel advance should have the potential for reduced environmental impact relative to the state of the art. Green Chemistry does not normally deal with research associated with 'end-of-pipe' or remediation issues.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.