Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts

Pavia, Cinzia; Giacalone, Francesco; Bivona, Lucia Anna; Salvo, Anna Maria Pia; Petrucci, Chiara; Strappaveccia, Giacomo; Vaccaro, Luigi; Aprile, Carmela; Gruttadauria, Michelangelo

doi:10.1016/j.molcata.2014.02.025

Cited by 39 publications

(21 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2-4 ppm, below the allowed limit value [42] (Table 9). The low residual of Pd in the products and the high activity over more runs is in agreement with the aforementioned "release and catch" mechanism [36,48].…”

Section: ′-Iodoacetophenonesupporting

confidence: 84%

“…CH3CN 84%), an alternative to conventional polar aprotic media, as a safer and easily recoverable reaction medium [15,48].…”

Section: Heck Reactionmentioning

confidence: 99%

“…It is known that a "release and catch" mechanism is operative for a PdNP-catalyzed Heck reaction [15,36,48] and that the required organic base strongly binds the soluble palladium species, facilitating their dissolution from the solid catalyst and consequently the leaching into the products. Besides, the base has the fundamental role of regenerating the active Pd(0) species [49], with the formation of the corresponding ammonium salt.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Immobilized Palladium Nanoparticles on Zirconium Carboxy-Aminophosphonates Nanosheets as an Efficient Recoverable Heterogeneous Catalyst for Suzuki–Miyaura and Heck Coupling

et al. 2017

Self Cite

View full text Add to dashboard Cite

Zirconium phosphate glycine diphosphonate nanosheets (ZPGly) have been used as support for the preparation of solid palladium nanoparticles, namely Pd@ZPGly. Thanks to the presence of carboxy-aminophosponate groups on the layer surface, ZPGly-based materials were able to stabilize a high amount of palladium (up to 22 wt %) also minimizing the amount of metal leached in the final products of representative important cross-coupling processes selected for proving the catalysts' efficiency. The catalytic systems have been fully characterized and used in low amounts (0.1 mol %) in the Suzuki-Miyaura and Heck cross-couplings. Moreover, the protocols were optimized for the use of recoverable azeotropic mixtures (aq. EtOH 96% or aq. CH 3 CN 84%, respectively) and in the flow procedure allowing one to isolate the final pure products, without any purification step, with very low residual palladium content and with a very low waste production.

show abstract

Section: ′-Iodoacetophenonesupporting

confidence: 84%

“…CH3CN 84%), an alternative to conventional polar aprotic media, as a safer and easily recoverable reaction medium [15,48].…”

Section: Heck Reactionmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Immobilized Palladium Nanoparticles on Zirconium Carboxy-Aminophosphonates Nanosheets as an Efficient Recoverable Heterogeneous Catalyst for Suzuki–Miyaura and Heck Coupling

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…These systems when compared to corresponding homogeneous ionic liquid phase show the general advantages of easy separation, recyclability, and they can be potentially applied in continuous processes. [38][39][40][41] In the present work, we have used such an approach in order to prepare two different materials based on multilayered covalentlylinked imidazolium or thiazolium salts on SBA-15 meso-structured silica. Herein, we investigate the use of supported imidazolium and thiazolium salts as catalysts for the etherification of benzylic alcohols.…”

Section: Introductionmentioning

confidence: 99%

Thiazolium‐Based Catalysts for the Etherification of Benzylic Alcohols under Solvent‐Free Conditions

et al. 2015

Self Cite

View full text Add to dashboard Cite

Thiazolium and imidazolium hybrid materials were prepared by radical reactions between a mercaptopropyl-modified SBA-15 mesoporous silica and bis-vinylthiazolium or bis-vinylimidazolium dibromide salts. These hybrid materials were characterized by several techniques and were employed in the etherification reaction of 1-phenylethanol. Solvent-free conditions at 160 8C under different gas phases (oxygen, air, nitrogen and argon) were used. The thiazolium-based material displayed excellent performances. Further studies were carried out using unsupported thiazolium salts, with or without a methyl group at the C-2 position of the thiazolium moiety. These studies allowed us to propose a reaction mechanism. The supported thiazolium-based material was successfully used in the etherification reaction of two other benzylic alcohols and also in seven consecutive cycles. This work represents the first use of thiazolium-based compounds as catalysts for the etherification reaction of alcohols.Scheme 1. Synthesis of SBA-15-Imi and SBA-15-Thia.

show abstract

“…In 2011, a new concept of heterogeneous materials based on highly cross-linked imidazolium salts anchored on silica gel as supports for palladium nanoparticles in high loadings was developed [80]. This topic was extended with the preparation of the material 137 as catalyst for the Heck reaction (Scheme 50) [81]. Material 137 was prepared by treatment of highly cross-linked imidazolium-based support 21a with an aqueous solution of Na2PdCl4, followed by reduction reaction with NaBH4 in ethanol.…”

Section: C-c Coupling Reactionsmentioning

confidence: 99%

Advances in Organic and Organic-Inorganic Hybrid Polymeric Supports for Catalytic Applications

2016

Self Cite

View full text Add to dashboard Cite

Abstract:In this review, the most recent advances (2014)(2015)(2016) on the synthesis of new polymer-supported catalysts are reported, focusing the attention on the synthetic strategies developed for their preparation. The polymer-supported catalysts examined will be organic-based polymers and organic-inorganic hybrids and will include, among others, polystyrenes, poly-ionic liquids, chiral ionic polymers, dendrimers, carbon nanotubes, as well as silica and halloysite-based catalysts. Selected examples will show the synthesis and application in the field of organocatalysis and metal-based catalysis both for non-asymmetric and asymmetric transformations.

show abstract

Evidences of release and catch mechanism in the Heck reaction catalyzed by palladium immobilized on highly cross-linked-supported imidazolium salts

Cited by 39 publications

References 51 publications

Immobilized Palladium Nanoparticles on Zirconium Carboxy-Aminophosphonates Nanosheets as an Efficient Recoverable Heterogeneous Catalyst for Suzuki–Miyaura and Heck Coupling

Immobilized Palladium Nanoparticles on Zirconium Carboxy-Aminophosphonates Nanosheets as an Efficient Recoverable Heterogeneous Catalyst for Suzuki–Miyaura and Heck Coupling

Thiazolium‐Based Catalysts for the Etherification of Benzylic Alcohols under Solvent‐Free Conditions

Advances in Organic and Organic-Inorganic Hybrid Polymeric Supports for Catalytic Applications

Contact Info

Product

Resources

About