Flow‐Based, Cerium Oxide Enhanced, Low‐Level Palladium Sonogashira and Heck Coupling Reactions by Perovskite Catalysts

Battilocchio, Claudio; Bhawal, Benjamin N.; Chorghade, Rajeev; Deadman, Benjamin J.; Hawkins, Joel M.; Ley, Steven V.

doi:10.1002/ijch.201300049

Cited by 17 publications

(9 citation statements)

References 81 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Apart from alumina and silica, ceria (CeO 2 ) has also been utilized to deposit palladium catalysts for cross‐coupling reactions in flow. Ley and coworkers utilized a low‐level palladium perovskite catalyst (LaFe 0.95 Pd 0.05 O 3 ) supported on ceria for continuous Sonogashira and Mizoroki–Heck reactions (Scheme ) 35. The packed‐bed reactor was prepared by simply mixing CeO 2 and the perovskite doped with palladium in a shaker before packing it into a column.…”

Section: Transition Metal‐catalyzed Cross Couplings In Continuous mentioning

confidence: 99%

“…Again, excellent conversions were achieved after a residence time of 20 min. Importantly, in order to avoid metal contamination of the product by palladium leaching, a column packed with metal‐scavenging resins had to be installed in the reactor for both the Sonogashira and Mizoroki–Heck flow setups 35…”

Section: Transition Metal‐catalyzed Cross Couplings In Continuous mentioning

confidence: 99%

“… General flow schemes for the LaFe 0.95 Pd 0.05 O 3 /CeO 2 catalyzed Sonogashira and Mizoroki–Heck coupling reactions 35. QP‐SA: Quadrapure TM sulfonic acid resin.…”

Section: Transition Metal‐catalyzed Cross Couplings In Continuous mentioning

confidence: 99%

See 2 more Smart Citations

Immobilized Transition Metals as Catalysts for Cross‐Couplings in Continuous Flow—A Critical Assessment of the Reaction Mechanism and Metal Leaching

2014

View full text Add to dashboard Cite

In the not too distant future many industrially important chemicals (including pharmaceuticals) will probably be manufactured using continuous flow technology. For a significant number of synthetic steps involved in these protocols transition metal (mostly palladium)‐catalyzed carbon–carbon or carbon–heteroatom bond forming reactions (“cross‐coupling chemistry”) will play an important role. Designing a process for continuous cross‐coupling chemistry involves either the use of a homogeneous or of a heterogeneous (immobilized) catalyst/ligand system. In the latter case, the catalyst/ligand system is typically in the form of a packed‐bed reactor, through which the reaction mixture is pumped, employing an appropriate temperature regime and residence time. Although this approach has been widely popular during the past 15 years, there is growing evidence that suggests that the use of immobilized transition metal catalysts for performing cross‐coupling chemistry in continuous flow is, in fact, not very practical. As demonstrated in this review, significant leaching of the transition metal out of the packed‐bed catalyst will almost inevitably occur, leading to decreased catalyst activity and contamination of the product with transition metal. This is a consequence of the well‐known fact that the reaction mechanism for these kinds of transformations is (quasi)homogeneous and involves the transformation of a Pd0 species into a (soluble) PdII species. Using an immobilized catalyst in a batch protocol the transient leaching of palladium will not be immediately obvious, as, after completion of the catalytic cycle, Pd0 will typically redeposit onto the support. In contrast, in continuous flow mode, the palladium metal will progressively be “chromatographed” through the packed‐bed catalyst until, ultimately, all palladium will be removed from the support. This effect typically will become only evident when long run experiments are performed. The preferred alternative, in particular for larger scale experiments, is to use a homogeneous (pre)catalyst in combination with an appropriate catalyst recycling technology.

show abstract

Section: Transition Metal‐catalyzed Cross Couplings In Continuous mentioning

confidence: 99%

Section: Transition Metal‐catalyzed Cross Couplings In Continuous mentioning

confidence: 99%

See 1 more Smart Citation

Immobilized Transition Metals as Catalysts for Cross‐Couplings in Continuous Flow—A Critical Assessment of the Reaction Mechanism and Metal Leaching

2014

View full text Add to dashboard Cite

show abstract

“…The catalyst effectively promoted coupling of aryl iodides with aryl acetylenes in good to excellent yields in a flow system for 24 h without any loss of catalytic activity (See Figure 26). [10] …”

Section: Perovskites Mediated Organic Transformationsmentioning

confidence: 99%

“…Several synthetic protocols like co‐precipitation, sol‐gel, solution combustion, and soft/hard templating methods have been developed for the design and development of these nanosized and porous perovskite oxide of chiselled size and shape. These perovskites based catalytic materials facilitate cross‐coupling, [10] acid/base [11] and selective oxidation reactions. [12, 13]…”

Section: Introductionmentioning

confidence: 99%

Modern Trends in the Applications of Perovskites for Selective Organic Transformations

Chandra

2021

ChemistrySelect

View full text Add to dashboard Cite

Perovskites have captivated the interest of contemporary synthetic chemists in both the academic and industrial sector due to their multifarious physicochemical properties like excellent thermal stability, oxygen mobility substitution of A and B cations. These perovskite based mixed metal oxides effectively promote selective organic transformations like selective oxidation reactions, selective hydrogenation reactions, nitro to amine reduction, carbon‐carbon and carbon hetero‐bond forming reactions. Furthermore, these mixed metal oxide perovskites have been investigated for the multi‐component domino reactions for synthesis of valuable organic compounds. Recently, metal halide perovskites have emerged as futuristic materials for the catalytic and photocatalytic selective organic transformations to form valuable organic compounds. The present review mainly addresses the recent developments in the catalytic and photocatalytic applications of perovkites in organic synthesis in the past 10 years.

show abstract

ChemInform Abstract: Flow‐Based, Cerium Oxide Enhanced, Low‐Level Palladium Sonogashira and Heck Coupling Reactions by Perovskite Catalysts.

et al. 2014

View full text Add to dashboard Cite

Flow-Based, Cerium Oxide Enhanced, Low-Level Palladium Sonogashira and Heck Coupling Reactions by Perovskite Catalysts. -A low-level palladium perovskite catalyst deposited on cerium oxide is efficiently employed for Pd-catalyzed Sonogashira and Heck cross-coupling reactions under continuous flow conditions. -(BATTILOCCHIO, C.; BHAWAL, B. N.; CHORGHADE, R.; DEADMAN, B. J.; HAWKINS, J. M.; LEY*, S. V.; Isr.

show abstract

Flow‐Based, Cerium Oxide Enhanced, Low‐Level Palladium Sonogashira and Heck Coupling Reactions by Perovskite Catalysts

Cited by 17 publications

References 81 publications

Immobilized Transition Metals as Catalysts for Cross‐Couplings in Continuous Flow—A Critical Assessment of the Reaction Mechanism and Metal Leaching

Immobilized Transition Metals as Catalysts for Cross‐Couplings in Continuous Flow—A Critical Assessment of the Reaction Mechanism and Metal Leaching

Modern Trends in the Applications of Perovskites for Selective Organic Transformations

ChemInform Abstract: Flow‐Based, Cerium Oxide Enhanced, Low‐Level Palladium Sonogashira and Heck Coupling Reactions by Perovskite Catalysts.

Contact Info

Product

Resources

About