Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes

Lo, Vanessa Kar‐Yan; Kung, Karen Ka‐Yan; Wong, Man Leung; Che, Chi‐Ming

doi:10.1016/j.jorganchem.2008.12.008

Cited by 125 publications

(49 citation statements)

References 73 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The target compounds possessing multiple bioactive moieties will afford a basis for the activity test of potential drug molecules. Terminal alkynes are widely used in click reaction [23][24][25][26][27], Glaser coupling reaction [38][39][40][41], Sonogashira reaction [42][43][44][45], dimerization [46], even different kinds of addition reactions to C-O and C-N bonds [47][48][49][50]. Thus, the obtained propargyl esters are also important intermediates for more 2(5H)-furanone derivatives with polyfunctional groups.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters

Tan

Wang

et al. 2011

Res Chem Intermed

View full text Add to dashboard Cite

Using K 2 CO 3 as a base and CH 3 CN as solvent, different kinds of N-[5-alkoxy-2(5H)-furanonyl] amino acids were reacted with propargyl bromide via substitution reaction at 40°C to give 16 N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters with the yields of 44-85% (mostly over 74%). The structures of all newly synthesized compounds were elucidated and confirmed by FTIR, UV, 1 H NMR, 13 C NMR, MS, and elemental analysis. The rapid, efficient, and brief synthesis of the series propargyl esters with multiple bioactive units, will afford not only a basis for the activity test of potential drug molecules, but also an important synthetic strategy for 2(5H)-furanone derivatives with polyfunctional groups.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis of N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters

Tan

Wang

et al. 2011

Res Chem Intermed

View full text Add to dashboard Cite

show abstract

“…and Hiyama [15][16][17] reactions, in the Larock heteroannulation reaction, [18][19][20][21] for the degradation of pollutants, 22 for hydrogenation 23 and in fuel cells. 24 In recent years, it has been proven that the use of complex functional groups, either graed or smeared onto solid supports, plays an important role in preventing the aggregation of metal catalysts.…”

Section: -14mentioning

confidence: 99%

C–C coupling reactions using a gold(iii) phosphorus complex confined within metal–organic framework fibers in aqueous solution

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Later heterogeneous catalytic methods were also described using e.g. a gold-based complex [16], silver-tungstenphosphoric acid [17], Cu(I) compound on silica [18] or on USY zeolite [19], Cu(II)-salt on hydroxyapatite [20].…”

Section: Copper-catalyzed Reactionsmentioning

confidence: 99%

Supported Metal Catalysts in Organic Syntheses

Kiss

Nemeth

Fodor

et al. 2015

Period. Polytech. Chem. Eng.

View full text Add to dashboard Cite

The importance of heterogeneous catalytic methods in organic syntheses is growing dynamically. Among the methods developed the supported metal catalysts take up an outstanding role. In this paper the results of the research group obtained in this field are reviewed. Keywords heterogeneous catalysis, supported metal catalysts, organic syntheses IntroductionMost organic syntheses require a catalyst for good conversion. With the exception of heterogeneous oxidation and reduction, these catalysts are mostly acids or bases. The traditional acids and bases have several disadvantageous properties, they are often dangerous, flammable, corrosive, or toxic, the workup of the reaction mixture is often tedious, producing high amounts of waste water, and the catalyst often decomposes during the workup procedure. These compounds or even their preparation is often harmful for the environment. Therefore in recent decades the development of heterogeneous catalytic methods became one of the main synthetic goals. The heterogeneous catalysts can eliminate the problems arising from the use of a homogeneous catalyst; they can be filtered out from the reaction mixture, simplifying this way the workup procedure, reducing the energy costs and decreasing the operation time as well as the amount of waste water. They are generally non-corrosive, non-toxic and often reusable or simply recyclable materials, and in some cases they can induce a considerable regio-even stereoselectivity. There were several minerals found in nature which showed excellent catalytic avtivity in organic syntheses. Based on these materials numerous mineralbased heterogeneous catalysts were developed in recent years not only for laboratory but also for industrial use. Thus, e.g. in a review published in 1999 about the heterogeneous catalytic industrial processes, 71 methods were presented which used natural, modified or artificial zeolites [1].These materials can also serve as supports of different metals. The acidic or basic properties of the support, their great surface as well as the fine dispersity of the metal on the support's surface can significantly increase the efficiency of these catalysts. Furthermore, the ligands which are often required for a homogeneous catalytic process, can be omitted in the heterogeneous methods, which can increase the atom efficiency of the process and make the workup of the reaction mixture easier.

show abstract

Gold(III) (C^N) complex-catalyzed synthesis of propargylamines via a three-component coupling reaction of aldehydes, amines and alkynes

Cited by 125 publications

References 73 publications

Synthesis of N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters

Synthesis of N-[5-alkoxy-2(5H)-furanonyl] amino acid propargyl esters

C–C coupling reactions using a gold(iii) phosphorus complex confined within metal–organic framework fibers in aqueous solution

Supported Metal Catalysts in Organic Syntheses

Contact Info

Product

Resources

About