Pd/C: An Efficient, Heterogeneous and Reusable Catalyst for Phosphane‐Free Carbonylative Suzuki Coupling Reactions of Aryl and Heteroaryl Iodides

Khedkar, Mayur V.; Tambade, Pawan J.; Qureshi, Ziyauddin S.; Bhanage, Bhalchandra M.

doi:10.1002/ejoc.201001134

Cited by 105 publications

(47 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The synthesis of esters and amides having certain biological activities in the field of organic synthesis, pesticides, agrochemicals and in the pharmaceuticals industry . Various Palladium‐based homogeneous and heterogeneous carbonylative methodologies have been reported for these reactions . However, most of the reported methods suffered from one or more disadvantages like harsh reaction conditions, longer time and use of phosphine ligands, co‐catalysts and additives.…”

Section: Resultsmentioning

confidence: 99%

Ionic Liquid Immobilized on Graphene‐Oxide‐Containing Palladium Metal Ions as an Efficient Catalyst for the Alkoxy, Amino, and Phenoxy Carbonylation Reactions

et al. 2018

Self Cite

View full text Add to dashboard Cite

The Immobilization of homogeneous metal catalysts onto the solid surface is an important challenge in the field of catalysis because these types of catalysts provide the homogeneous nature as well as reusability of catalysts. In this report, novel Palladium ion containing ionic liquid immobilized onto graphene oxide (Pd@GOIL) and characterized using various analytical techniques like FT‐IR, XPS, TGA, SEM, TEM, BET and EXAFS analysis. This synthesized material acts as a highly efficient catalyst for the alkoxycarbonylation, aminocarbonylation and phenoxycarbonylation reactions from easily available aryl iodides. Effect of various reaction parameters like CO pressure, base, solvent, the effect of time and temperature using Pd@GOIL catalyst were examined. This catalyst also tolerates the wide variety of substrates with the effective electronic factor. Specifically, this catalyst shows excellent catalytic performance towards the esterification and amidation without the need of any ligands, co‐catalysts and additives. Additionally, the catalyst shows superior recyclability up to eight recycle runs without discernible activity and selectivity deterioration.

show abstract

Section: Resultsmentioning

confidence: 99%

Ionic Liquid Immobilized on Graphene‐Oxide‐Containing Palladium Metal Ions as an Efficient Catalyst for the Alkoxy, Amino, and Phenoxy Carbonylation Reactions

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…[16] In continuation of our ongoing research on the development of new facile phosphine-free protocols for carbonylation reactions, [17] herein we firstly report a heterogeneous, phosphine-free and recyclable protocol for the synthesis of N-substituted phthalimides from range of precursors such as o-dihaloarenes, o-halobenzoates and o-halobenzoic acids using Pd/C as a catalyst (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Palladium on Carbon: An Efficient, Heterogeneous and Reusable Catalytic System for Carbonylative Synthesis of N‐Substituted Phthalimides

et al. 2011

Self Cite

View full text Add to dashboard Cite

The application of palladium on carbon (Pd/C) as a heterogeneous recyclable catalyst was investigated for the double carbonylation of o-dihaloarenes with amines providing excellent yield of Nsubstituted phthalimides in shorter reaction time as compared to earlier reported homogeneous protocols. Furthermore, the scope of the developed protocol was applied for the synthesis N-substituted phthalimides from o-halobenzoates and o-halobenzoic acid via a single step carbonylative cyclization reaction. The developed methodology describes an efficient one-step approach for the synthesis of an important class of heterocycles and tolerates a wide variety of functional groups. It circumvents the use of phosphine ligands with an additional advantage of catalyst recyclability for up to eight consecutive cycles.

show abstract

“…The term 'carbonylation', coined by Reppe in the '30s, includes a plethora of reactions 1 such as formylation, 2 hydroformylation, alkoxycarbonylation, 3,4 aminocarbonylation, [5][6][7] carbonylative Heck, 8 carbonylative Suzuki Miyaura, 9 carbonylative Sonogashira reactions, [10][11] which provide an easy and practical method for the introduction of a carbonyl group into an organic substrate.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Microwave-Assisted CO Aminocarbonylation with a Recyclable Pd(II)/TPP-β-Cyclodextrin Cross-Linked Catalyst

Gaudino

Carnaroglio

Martina

et al. 2015

Org. Process Res. Dev.

View full text Add to dashboard Cite

The incorporation of the carbonyl moiety into organic molecules using a three-component matrix, including carbon monoxide, an organic halide and a nucleophilic component offers a simple and versatile approach to the formation of carboxylic acids, anhydrides, esters, amides and ketones. The design of a sustainable synthetic protocol for aminocarbonylation can be efficiently accomplished using a multi-faceted strategy that combines solid green catalysts and suitable enabling techniques. The safe and synergistic use of carbon monoxide in a microwave reactor under pressure may be able to create a technological breakthrough in aminocarbonylation reactions. Moreover, a new recyclable catalytic system "CβCAT" based on Pd(II)-triphenylphosphine embedded in cross linked β-cyclodextrin (hexamethylene diisocyanate) has been found to be very efficient in aryl iodide aminocarbonylation reactions.

show abstract

Pd/C: An Efficient, Heterogeneous and Reusable Catalyst for Phosphane‐Free Carbonylative Suzuki Coupling Reactions of Aryl and Heteroaryl Iodides

Cited by 105 publications

References 29 publications

Ionic Liquid Immobilized on Graphene‐Oxide‐Containing Palladium Metal Ions as an Efficient Catalyst for the Alkoxy, Amino, and Phenoxy Carbonylation Reactions

Ionic Liquid Immobilized on Graphene‐Oxide‐Containing Palladium Metal Ions as an Efficient Catalyst for the Alkoxy, Amino, and Phenoxy Carbonylation Reactions

Palladium on Carbon: An Efficient, Heterogeneous and Reusable Catalytic System for Carbonylative Synthesis of N‐Substituted Phthalimides

Highly Efficient Microwave-Assisted CO Aminocarbonylation with a Recyclable Pd(II)/TPP-β-Cyclodextrin Cross-Linked Catalyst

Contact Info

Product

Resources

About