Dramatic Impact of ppb Levels of Palladium on the “Copper‐Catalyzed” Sonogashira Coupling

Gonda, Zsombor; Tolnai, Gergely L.; Novàk, Zoltán

doi:10.1002/chem.201001880

Cited by 85 publications

(39 citation statements)

References 67 publications

(26 reference statements)

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“…34,35 So, two control experiments was done using 5 mol% of FeCl 3 .6H 2 O or Fe(NO 3 ) 3 .9H 2 O as catalyst between phenol and bromobenzene under the optimized reaction conditions. 34,35 So, two control experiments was done using 5 mol% of FeCl 3 .6H 2 O or Fe(NO 3 ) 3 .9H 2 O as catalyst between phenol and bromobenzene under the optimized reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

Application of nickel ferrite and cobalt ferrite magnetic nanoparticles in C–O bond formation: a comparative study between their catalytic activities

2015

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Magnetic nanoparticles of nickel ferrite and cobalt ferrite were synthesized and their catalytic activity in the C-O bond formation reaction was compared. Both these spinel systems can catalyze the reaction between various types of aryl halides and phenol derivatives efficiently. The catalysts are easily removed from the reaction medium and can be reused further in several runs. All the reactions resulted in very good to excellent yields under optimized reaction conditions; however, reactions using nickel ferrite as catalyst were completed in relatively shorter reaction times. Also, analyses showed that reusability of the two catalytic systems approximately are comparable. Scheme 2. a) Recovery and reuse of nickel ferrite nanoparticles; and b) Recovery and reuse of cobalt ferrite nanoparticles.Reaction conditions: bromobenzene (1 mmol), phenol (1.1 mol), catalyst (5 mol %), K2CO3 (1.2 mmol), DMF (2 ml) and reaction stirred at 80 °C.

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Section: Resultsmentioning

confidence: 99%

Application of nickel ferrite and cobalt ferrite magnetic nanoparticles in C–O bond formation: a comparative study between their catalytic activities

2015

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“…In line with this, Novák et al [153] unambiguously proved that ppb levels of Pd impurities had a dramatic effect on the efficiency of the ''Cu-catalyzed'' Sonogashira reaction. Despite the propensity of Ni to form π-complexes with acetylenic C≡C bonds and consequently become inactivated [13], a Ni-catalyzed Sonogashira coupling has successfully been conducted with activated aryl iodides and aromatic terminal alkynes using a catalytic Ni/Cu dyad with K 2 CO 3 as the base (Scheme 9.17) [154].…”

Section: Alkynylations Catalyzed By Other Transition Metalsmentioning

confidence: 56%

Cross‐Coupling Reactions to sp Carbon Atoms

Schaub

Kivala

2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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“…On the other hand, it is found previously that the presence of metal contaminants presented in the iron source can catalyze these reactions [34,35]. So, in order to verify that this phenomenon does not affect the reaction, a control experiment was done using 10 mol% of FeCl 3 as catalyst under the optimized reaction conditions.…”

Section: ((Scheme 4))mentioning

confidence: 98%