Palladium complexes of heterobidentate ligands: Active catalysts for direct acylation of aryl halides with aldehydes via C(sp 2 )-H activation

Saikia, Kokil; Dutta, Dipak Kumar

doi:10.1016/j.molcata.2015.07.007

Cited by 6 publications

(1 citation statement)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These functional arms exploit their intrinsic flexibility adopting different most stable conformations depending on the nature of target, i.e., solvent molecules in 3 (Figures S8−S10), Pd 2+ in 4 (Figures 3c,d and S11) or both Pd 2+ cations and Pd 0 1 SACs in 5 (Figures 3e,f, 4, and S14). The Pd 2+ −S bond distances [1.96(4) and 2.17(2) Å ( 4)] (Figures 3d and S13a) are close enough to those observed previously, 65 and similar to the Pd 0 −S bond distance observed in 5 2.16(2) Å] (Figures 3f and S13b). In 3−5 the thioether chains from the Mecysmox ligand show as basic conformation one of the two distinct moieties in a distended conformation toward the center of the pores, and the other one regularly bent, with the terminal methyl groups pointing toward the smaller interstitial voids residing along the a-axis (Figures S10 and S14).…”

Section: ■ Introductionsupporting

confidence: 87%

Soluble/MOF-Supported Palladium Single Atoms Catalyze the Ligand-, Additive-, and Solvent-Free Aerobic Oxidation of Benzyl Alcohols to Benzoic Acids

et al. 2021

View full text Add to dashboard Cite

Metal single-atom catalysts (SACs) promise great rewards in terms of metal atom efficiency. However, the requirement of particular conditions and supports for their synthesis, together with the need of solvents and additives for catalytic implementation, often precludes their use under industrially viable conditions. Here, we show that palladium single atoms are spontaneously formed after dissolving tiny amounts of palladium salts in neat benzyl alcohols, to catalyze their direct aerobic oxidation to benzoic acids without ligands, additives, or solvents. With this result in hand, the gram-scale preparation and stabilization of Pd SACs within the functional channels of a novel methyl-cysteine-based metal−organic framework (MOF) was accomplished, to give a robust and crystalline solid catalyst fully characterized with the help of single-crystal X-ray diffraction (SCXRD). These results illustrate the advantages of metal speciation in ligand-free homogeneous organic reactions and the translation into solid catalysts for potential industrial implementation.Article pubs.acs.org/JACS

show abstract

Section: ■ Introductionsupporting

confidence: 87%

Soluble/MOF-Supported Palladium Single Atoms Catalyze the Ligand-, Additive-, and Solvent-Free Aerobic Oxidation of Benzyl Alcohols to Benzoic Acids

et al. 2021

View full text Add to dashboard Cite

show abstract

Selective C(sp³)–H Monoarylation Catalyzed by a Covalently Cross‐Linked Reverse Micelle‐Supported Palladium Catalyst

Hoyt

Lee

et al. 2017

Adv Synth Catal

View full text Add to dashboard Cite

In this work, we illustrate the performance of as olvated micelle-supported liganda saplatform for coordination with palladium for C-H arylation. Themicelle-supported ligandiso ne of the first applications of am icelle-supported ligand for C-H arylation, andprovides atunable support for future elaboration. Theu se of as patially constrained systemp ro-moted selectivity trends influenced by botht he sterics and electronics of the system, differing from the homogeneous catalyst, with high yields and selectivities.

show abstract

Co (II)‐C12 alkyl carbon chain multi‐functional ionic liquid immobilized on nano‐SiO₂ nano‐SiO₂@CoCl₃‐C12IL as an efficient cooperative catalyst for C–H activation by direct acylation of aryl halides with aldehydes

2017

Applied Organom Chemis

View full text Add to dashboard Cite

Nano‐silica supported ionic liquids composed of alkyl carbon chain and transition metal chlorides anions have been prepared and successfully applied as a heterogeneous catalyst in the direct aldehyde C‐H activation. Catalytic results indicated that nano‐SiO2 supported ionic liquid consisting C12 alkyl carbon chain and CoCl3 anion nano‐SiO2@CoCl3‐C12IL showed excellent catalytic properties with good to excellent yields towards the desired aryl ketones. The excellent recyclability of the supported catalyst, mild reaction conditions, low catalyst loading, and operational simplicity are the important features of this methodology.

show abstract

Palladium complexes of heterobidentate ligands: Active catalysts for direct acylation of aryl halides with aldehydes via C(sp 2 )-H activation

Cited by 6 publications

References 41 publications

Soluble/MOF-Supported Palladium Single Atoms Catalyze the Ligand-, Additive-, and Solvent-Free Aerobic Oxidation of Benzyl Alcohols to Benzoic Acids

Soluble/MOF-Supported Palladium Single Atoms Catalyze the Ligand-, Additive-, and Solvent-Free Aerobic Oxidation of Benzyl Alcohols to Benzoic Acids

Selective C(sp³)–H Monoarylation Catalyzed by a Covalently Cross‐Linked Reverse Micelle‐Supported Palladium Catalyst

Co (II)‐C12 alkyl carbon chain multi‐functional ionic liquid immobilized on nano‐SiO₂ nano‐SiO₂@CoCl₃‐C12IL as an efficient cooperative catalyst for C–H activation by direct acylation of aryl halides with aldehydes

Contact Info

Product

Resources

About

Palladium complexes of heterobidentate ligands: Active catalysts for direct acylation of aryl halides with aldehydes via C(sp 2 )-H activation

Cited by 6 publications

References 41 publications

Soluble/MOF-Supported Palladium Single Atoms Catalyze the Ligand-, Additive-, and Solvent-Free Aerobic Oxidation of Benzyl Alcohols to Benzoic Acids

Soluble/MOF-Supported Palladium Single Atoms Catalyze the Ligand-, Additive-, and Solvent-Free Aerobic Oxidation of Benzyl Alcohols to Benzoic Acids

Selective C(sp3)–H Monoarylation Catalyzed by a Covalently Cross‐Linked Reverse Micelle‐Supported Palladium Catalyst

Co (II)‐C12 alkyl carbon chain multi‐functional ionic liquid immobilized on nano‐SiO2 nano‐SiO2@CoCl3‐C12IL as an efficient cooperative catalyst for C–H activation by direct acylation of aryl halides with aldehydes

Contact Info

Product

Resources

About

Selective C(sp³)–H Monoarylation Catalyzed by a Covalently Cross‐Linked Reverse Micelle‐Supported Palladium Catalyst

Co (II)‐C12 alkyl carbon chain multi‐functional ionic liquid immobilized on nano‐SiO₂ nano‐SiO₂@CoCl₃‐C12IL as an efficient cooperative catalyst for C–H activation by direct acylation of aryl halides with aldehydes