Crystal structure of a novel polymorph of trans-dichlorobis (triphenylphosphine) palladium (II) and its application as a novel, efficient and retrievable catalyst for the amination of aryl halides and stille cross-coupling reactions

Naghipour, Ali; Ghorbani‐Choghamarani, Arash; Babaee, Heshmatollah; Hashemi, Mojdeh Sadat; Notash, Behrouz

doi:10.1016/j.jorganchem.2016.10.002

Cited by 16 publications

(4 citation statements)

References 27 publications

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“… Entry Catalyst Condition reaction Yield (%) Refs. 1 PdCl 2 (PPh 3 ) 2 PEG, Na 2 CO 3 ,90 °C 82 62 2 Pd NPs PEG, K 2 CO 3 , H 2 O, 80 °C 90 63 3 Pd(OAc) 2 Dabco, Bu 4 NF, dioxane, 80 °C 93 64 4 Pd4 peptide KOH, EtOH/H 2 O, 25 °C 100 61 5 Pd@BTU-GO NaOAc, PEG-400, 25 °C 94 17 6 HMS–CPTMS–Cy–Pd PEG, K 2 CO 3 , 100 °C 95 65 7 G 3 DenP-Ni CsF, H 2 O, N 2 atm 98 66 8 Pd/Fe 3 O 4 CsF, dioxane, 100 °C 86 67 9 Pd NPs /C@Fe 3 O 4 DMF, K 2 CO 3 , 100 °C, 25 °C …”

Section: Resultsmentioning

confidence: 99%

A novel strategy for stabilization of sub-nanometric Pd colloids on kryptofix functionalized MCM-41: nanoengineered material for Stille coupling transformation

Alamgholiloo

Pesyan

Rostamnia

2021

Sci Rep

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The stabilization of sub-nanometric metal particles (< 1 nm) with suitable distribution remained challenging in the catalytic arena. Herein, an intelligent strategy was described to anchoring and stabilizing sub-nanometric Pd colloids with an average size of 0.88 nm onto Kryptofix 23 functionalized MCM-41. Then, the catalytic activity of Pd@Kryf/MCM-41 was developed in Stille coupling reaction with a turnover frequency (TOF) value of 247 h−1. The findings demonstrate that porous MCM-41 structure and high-affinity Kryptofix 23 ligand toward adsorption of Pd colloids has a vital role in stabilizing the sub-nanometric particles and subsequent catalytic activity. Overall, these results suggest that Pd@Kryf/MCM-41 is a greener, more suitable option for large-scale applications and provides new insights into the stabilization of sub-nanometric metal particles.

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Section: Resultsmentioning

confidence: 99%

A novel strategy for stabilization of sub-nanometric Pd colloids on kryptofix functionalized MCM-41: nanoengineered material for Stille coupling transformation

Alamgholiloo

Pesyan

Rostamnia

2021

Sci Rep

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“…These procedures were developed because no palladium system has been reported to catalyze the most preferable reaction: the coupling of aqueous ammonia with aryl halides and a simple hydroxide base (Figure 1c). 5 Aqueous ammonia would be the ideal source because it is readily available, less expensive than organic solutions of ammonia, and easier to handle and store safely than anhydrous ammonia. However, the palladium-catalyzed amination of aryl halides with aqueous ammonia is difficult to achieve.…”

Section: ■ Introductionmentioning

confidence: 99%

Palladium-Catalyzed Amination of Aryl Halides with Aqueous Ammonia and Hydroxide Base Enabled by Ligand Development

Choi,

Brunn,

Borate

et al. 2024

J. Am. Chem. Soc.

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The conversion of aryl halides to primary arylamines with a convenient and inexpensive source of ammonia has been a long-standing synthetic challenge. Aqueous ammonia would be the most convenient and least expensive form of ammonia, but such a palladium-catalyzed amination reaction with a high concentration of water faces challenges concerning catalyst stability and competing hydroxylation, and palladium-catalyzed reactions with this practical reagent are rare. Further, most reactions with ammonia to form primary amines are conducted with tert-butoxide base, but reactions with ammonium hydroxide would contain hydroxide as base. Thus, ammonia surrogates, ammonia in organic solvents, and ammonium salts have been used under anhydrous conditions instead with varying levels of selectivity for the primary amine. We report the palladium-catalyzed amination of aryl and heteroaryl chlorides and bromides with aqueous ammonia and a hydroxide base to form the primary arylamine with high selectivity. The palladium catalyst containing a new dialkyl biheteroaryl phosphine ligand (KPhos) suppresses both the formation of aryl alcohol and diarylamine side products. Mechanistic studies with a soluble hydroxide base revealed turnover-limiting reductive elimination of the arylamine and an equilibrium between arylpalladium amido and hydroxo complexes prior to the turnover-limiting step.

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“…To screen the catalytic properties of the synthesized complexes, Pd(II) complexes catalyzed three‐component coupling reaction of aldehydes, amines and phenylacetylenes under solvent free conditions in ionic liquid at 80 °C to give propargylamines in high yields . Trans [PdCl 2 (PPh 3 ) 2 ] complex was synthesized, characterized and applied by Ali Naghipour and coworker as an efficient catalyst for the amination of aryl halides to afford primary amines and also in the catalytic Stille cross‐coupling reaction with satisfactory results A. M. Trzeciak.…”

Section: Introductionmentioning

confidence: 99%

Preparation of novel palladium nanoparticles supported on magnetic iron oxide and their catalytic application in the synthesis of 2‐imino‐3‐phenyl‐2,3‐dihydrobenzo[d]oxazol‐5‐ols

Habibi

Heydari

Afsharfarnia

et al. 2018

Applied Organom Chemis

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Novel Pd nanoparticles were prepared in five successive stages: 1) preparation of the Fe3O4 magnetic nanoparticles (Fe3O4 MNPs), 2) coating of Fe3O4 MNPs with SiO2 (Fe3O4@SiO2), 3) functionalization of Fe3O4@SiO2 with 3‐chloropropyltrimethoxy‐ silane (CPTMS) ligand (Fe3O4@SiO2@CPTMS), 4) further functionalization with 3,5‐diamino‐1,2,4‐triazole (DAT) ligand (Fe3O4@SiO2@CPTMS @DAT), and 5) the complexation of Fe3O4@SiO2@CPTMS@DAT with PdCl2 (Fe3O4@SiO2@CPTMS@ DAT@Pd). Then, the obtained Pd nano‐catalyst characterized by different methods such as the elemental analysis (CHN), FT‐IR, XRD, EDX, SEM, TEM, TG‐DTA and VSM. Finally, the Pd catalyst was applied for the synthesis of various 2‐imino‐3‐phenyl‐2,3‐dihydrobenzo[d]oxazol‐5‐ols.

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Crystal structure of a novel polymorph of trans-dichlorobis (triphenylphosphine) palladium (II) and its application as a novel, efficient and retrievable catalyst for the amination of aryl halides and stille cross-coupling reactions

Cited by 16 publications

References 27 publications

A novel strategy for stabilization of sub-nanometric Pd colloids on kryptofix functionalized MCM-41: nanoengineered material for Stille coupling transformation

A novel strategy for stabilization of sub-nanometric Pd colloids on kryptofix functionalized MCM-41: nanoengineered material for Stille coupling transformation

Palladium-Catalyzed Amination of Aryl Halides with Aqueous Ammonia and Hydroxide Base Enabled by Ligand Development

Preparation of novel palladium nanoparticles supported on magnetic iron oxide and their catalytic application in the synthesis of 2‐imino‐3‐phenyl‐2,3‐dihydrobenzo[d]oxazol‐5‐ols

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