Copper(I) Zeolites as Heterogeneous and Ligand‐Free Catalysts: [3+2] Cycloaddition of Azomethine Imines

Keller, Michel; Sido, Abdelkarim Sani Souna; Pale, Patrick; Sommer, Jean

doi:10.1002/chem.200802191

Cited by 107 publications

(44 citation statements)

References 37 publications

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“…This Cu I zeolite-catalyzed reaction provided a rapid, regio-and stereoselective access to complex pyrazolidinone derivatives [22].…”

Section: Unauthenticatedmentioning

confidence: 99%

“…In analogy with the mechanism of the Cu I zeolitecatalyzed [3+2]-cycloaddition of azomethine imines with terminal alkynes (Scheme 4), established through labeled substrates and zeolites [22], the in situ formation of acetylides can be envisaged due to the presence of amino derivatives, which may act as bases toward the alkynes coordinated to Cu I zeolites (Scheme 6; (c)). These results have thus demonstrated that Cu I zeolites act as dual catalysts in such multicomponent reactions.…”

Section: Unauthenticatedmentioning

confidence: 99%

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Metal-doped Zeolites as Green Catalysts for Organic Synthesis

Chassaing

Alix

Olmos

et al. 2010

Zeitschrift Für Naturforschung B

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Metal-doped zeolites prepared by vapor diffusion are excellent heterogeneous catalysts. Copper(I)-exchanged zeolites catalyze for example 1,3-dipolar reactions or Mannich condensation, whereas scandium(III)-exchanged zeolites catalyze the Mukaiyama-type aldolization. These catalysts are easily prepared, stable for months, conveniently recovered by filtration and recyclable. They can be used in safe solvents and even without solvent, and thus fully comply with the Green Chemistry principles. Their ease of handling and their large scope of applications enabled us to introduce the "zeo-click" concept for organic synthesis catalyzed by such green heterogeneous catalysts.

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“…This Cu I zeolite-catalyzed reaction provided a rapid, regio-and stereoselective access to complex pyrazolidinone derivatives [22].…”

Section: Unauthenticatedmentioning

confidence: 99%

Section: Unauthenticatedmentioning

confidence: 99%

Metal-doped Zeolites as Green Catalysts for Organic Synthesis

Chassaing

Alix

Olmos

et al. 2010

Zeitschrift Für Naturforschung B

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“…This zeolite was selected first, since upon metal doping, it proved efficient for other organic transformations [24][25][26] and because it holds large pores, able to accommodate several molecules together.…”

Section: Resultsmentioning

confidence: 99%

“…This relative lack led us to consider applying metal-doped zeolites as catalysts for such cycloadditions (Scheme 2), in connection with our recent zeo-click syntheses. [25][26][27][28] We indeed recently demonstrated that Cu I zeolites are very effective and reusable catalysts for the cycloaddition of alkynes with azides or azomethine imines (Scheme 3a and b). [25,26] Therefore, other cycloadditions, such as the reaction of N-arylimines with alkenes should be amenable under similar conditions.…”

Section: Introductionmentioning

confidence: 99%

“…[25][26][27][28] We indeed recently demonstrated that Cu I zeolites are very effective and reusable catalysts for the cycloaddition of alkynes with azides or azomethine imines (Scheme 3a and b). [25,26] Therefore, other cycloadditions, such as the reaction of N-arylimines with alkenes should be amenable under similar conditions. Moreover, we also showed that one-pot multicomponent reactions could also be catalyzed by Cu I zeolites (Scheme 3c).…”

Section: Introductionmentioning

confidence: 99%

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Scandium(III) Zeolites as New Heterogeneous Catalysts: [4+2]Cyclocondensation of in situ Generated Aryl Imines with Alkenes

Olmos

Sommer

Pale

2011

Chemistry A European J

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Scandium(III)-exchanged zeolite was used as heterogeneous ligand-free catalysts for the [4+2]cyclocondensation of amines and aldehydes with alkenes through the in situ formation of imines. Such catalysts offered a versatile, efficient, and highly regio- and stereoselective synthesis of tetrahydroquinoline derivatives. These catalysts exhibited a wide scope and compatibility with functional groups. They are very simple to use, easy to remove (by simple filtration), and they are recyclable (up to three times without loss of activity).

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[3 + 2] Cycloadditions of Azomethine Imines

Grošelj

Svete

2020

Organic Reactions

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In spite of their late discovery in the middle of 20 th century, the importance of azomethine imines and their [3+2] cycloaddition reactions has grown constantly throughout the decades. Today, [3+2] cycloadditions of azomethine imines have become indispensable in the preparation of pyrazole derivatives with all degrees of saturation. The structural diversity of azomethine imines is wide and comprises acyclic, C , N ‐cyclic, N , N ‐cyclic, and C , N , N ‐cyclic 1,3‐dipoles. Although electron‐deficient dipolarophiles are preferred, electron‐rich dipolarophiles, such as enol ethers and enamines, are also commonly used in these reactions. Compared to cyclocondensation methods and [3+2] cycloadditions with diazoalkanes and nitrile imines, [3+2] cycloadditions with azomethine imines provide access to a greater diversity of pyrazole derivatives with all degrees of saturation. As with other 1,3‐dipolar cycloadditions, a concerted and nearly synchronous mechanism has been proposed for most [3+2] cycloadditions of azomethine imines, although a stepwise mechanism may be viable in some cases. Several examples of asymmetric [3+2] cycloadditions of azomethine imines that afford non‐racemic cycloadducts with high enantioselectivity have been reported. These asymmetric cycloadditions are performed with various types of transition metal catalysts and organocatalysts, and indicate their potential for the asymmetric synthesis of saturated pyrazole derivatives. Finally, many examples of copper‐catalyzed and thermal, strain‐promoted [3+2] cycloadditions of azomethine imines (in particular sydnones) clearly indicate wide applicability of these reactions in bioconjugation, fluorescent labelling, materials functionalization, and other applications outside the realm of pure organic synthesis.

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Copper(I) Zeolites as Heterogeneous and Ligand‐Free Catalysts: [3+2] Cycloaddition of Azomethine Imines

Cited by 107 publications

References 37 publications

Metal-doped Zeolites as Green Catalysts for Organic Synthesis

Metal-doped Zeolites as Green Catalysts for Organic Synthesis

Scandium(III) Zeolites as New Heterogeneous Catalysts: [4+2]Cyclocondensation of in situ Generated Aryl Imines with Alkenes

[3 + 2] Cycloadditions of Azomethine Imines

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