A Well‐Defined Complex for Palladium‐Catalyzed Aerobic Oxidation of Alcohols: Design, Synthesis, and Mechanistic Considerations

Jensen, David R.; Schultz, Mitchell J.; Mueller, Jaime A.; Sigman, Matthew S.

doi:10.1002/anie.200351997

Cited by 299 publications

(112 citation statements)

References 23 publications

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“…Therefore, we performed some additional experiments to compare more directly the efficiency of the various catalysts. Determination of the conversion curves under our reaction conditions ( Figure 3) revealed that complex 1 was indeed the most efficient catalyst for this reaction, with an initial activity almost two times higher than that of both PdA C H T U N G T R E N N U N G (OAc) 2 and monocarbene palladium complex 2, [16] which expectedly forms Nolans bis(trifluoroacetate) complex in situ. After five hours of reaction, PdA C H T U N G T R E N N U N G (OAc) 2 gave only 37 % conversion with 92 % selectivity for the Z product, while complex 2 gave 31 % conversion with 94 % selectivity.…”

Section: Resultsmentioning

confidence: 85%

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Highly Efficient Alkyne Hydroarylation with Chelating Dicarbene Palladium(II) and Platinum(II) Complexes

et al. 2008

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We report on a novel reaction protocol for the coupling of arenes with alkynes (the Fujiwara reaction), yielding products of formal trans-hydroarylation of the triple bond. The protocol makes use of a chelating N-heterocyclic dicarbene palladium(II) complex as catalyst and allows us to perform the reaction in a few hours with only 0.1 mol % catalyst yielding the trans-hydroarylation product in high yields and with excellent selectivity. We discuss the applicability of this reaction protocol, which appears at present quite general with respect to the alkyne, albeit limited to electron-rich arenes. We also present the results of catalyst optimisation with respect to the nature of the nitrogen substituents in the carbene units, of the bridging group between the carbene units and of the coordinated anionic ligands. Finally, we also discuss the catalytic performance of a related chelating dicarbene complex of platinum(II).

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Section: Resultsmentioning

confidence: 85%

“…The reagents were purchased by Aldrich as high-purity products and generally used as received. Complexes 2, [16] 4, [18] 5, [19] [b] In parentheses the yield in the hydrolysed product. Reaction conditions: see Experimental Section.…”

Section: Experimental Section General Remarksmentioning

confidence: 99%

Highly Efficient Alkyne Hydroarylation with Chelating Dicarbene Palladium(II) and Platinum(II) Complexes

et al. 2008

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“…These properties have led to a number of applications where NHC-based catalysts exhibit superior performance. Such NHC-metal complexes have been successfully utilized in cross-coupling reactions [16] and related processes, including hydrogenation [17], hydroformylation [18] hydrosilylation [19], oxidation [20], metathesis [21], cycloisomerisation of olefins [22], the synthesis of furans [23] and cyclopropanation reactions.…”

Section: Introductionmentioning

confidence: 99%

Polyimide-Supported Dichloro-1,3-bis(p-dimethylaminobenzyl)benzimidazolidin-2-ilidenruthenium (II) as Effective Catalyst for Hydrosilylation Reactions

Köytepe

Seçki̇n

Yaşar

et al. 2008

Designed Monomers and Polymers

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The present study relates to a heterogeneous polyimide-supported transition metal complex catalyst for hydrosilylation reactions, which is prepared by functionalizing a heat-and acid-resistant polyimide resin with a homogeneous metal catalyst of ruthenium (II) complex. The heterogeneous polyimide-supported transition metal complex catalyst of the invention provides superior catalytic activity, selectivity and stability in the hydrosilylation of acetophenone. Further, the catalyst has strong resistance against heat and acid. Besides, the catalyst of the invention may provide the following advantage which are critical in industrial use: it can be easily separated from the reaction product, which eases recycling of the catalyst.

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“…Accordingly, variety of transition metal based catalysts (mainly cobalt, vanadium, ruthenium and palladium) has been intensively investigated for aerobic oxidation of alcohols so far. [77][78][79][80] Although metalloporphyrins have been used to catalyze the oxidation of alcohols with PhIO, t-BuOOH, KHSO 5 and m-CPBA (m-chloroperbenzoic acid) as oxidants, [81][82][83][84] few studies on metalloporphyrins-catalyzed oxidation of alcohols by molecular oxygen were reported. For examples, Woo and co-authors ever reported the aerobic homogeneous oxidation of benzyl alcohol with oxotitanium porphyrin (TTP)Ti=O (TTP=meso-tetra-p-tolylporphyrin), which gave benzaldehyde in modest yields (48%) after 94 hours in refluxing chlorobenzene.…”

Section: Oxidation Of Alcoholsmentioning

confidence: 99%

Biomimetic Homogeneous Oxidation Catalyzed by Metalloporphyrins with Green Oxidants

Ji¹,

Zhou²

2010

Biomimetics Learning From Nature

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Cytochrome P-450 mono-oxygenase enzymes play a key role in the oxidative transformation in living systems. As one kind of cytochrome P-450 models, metalloporphyrins have been widely used in selective oxygenation of hydrocarbons under mild conditions. The chapter focuses on reviewing the biomimetic homogeneous oxidation of organic compounds catalyzed by metalloporphyrins with green oxidants such as dioxygen or hydrogen peroxide, in which the oxidized substrates include alkanes, olefins, alcohols, aldehydes, sulfides etc. The mechanisms for the oxidation of different substrates were also described. We can assume that the coming decade is going to be dedicated to the development of metalloporphyrins biomimetic catalyst in petrochemical and fine chemical industries.

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A Well‐Defined Complex for Palladium‐Catalyzed Aerobic Oxidation of Alcohols: Design, Synthesis, and Mechanistic Considerations

Cited by 299 publications

References 23 publications

Highly Efficient Alkyne Hydroarylation with Chelating Dicarbene Palladium(II) and Platinum(II) Complexes

Highly Efficient Alkyne Hydroarylation with Chelating Dicarbene Palladium(II) and Platinum(II) Complexes

Polyimide-Supported Dichloro-1,3-bis(p-dimethylaminobenzyl)benzimidazolidin-2-ilidenruthenium (II) as Effective Catalyst for Hydrosilylation Reactions

Biomimetic Homogeneous Oxidation Catalyzed by Metalloporphyrins with Green Oxidants

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