Application of palladacycles in Heck type reactions

Herrmann, Wolfgang A.; Böhm, Volker P. W.; Reisinger, Claus‐Peter

doi:10.1016/s0022-328x(98)01050-x

Cited by 560 publications

(130 citation statements)

References 103 publications

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“…[61] For the Heck coupling shown in Scheme 3, the air-stable but highly reactive [(tBu) 3 PH]BF 4 phosphonium salt described by Netherton and Fu [62] was employed as a ligand precursor using the palladacycle [63] developed by Herrmann et al as the palladium precatalyst. Depending on the reactivity of the aryl chloride, 1.5-10 mol % of Pd catalyst (3-20 % of ligand), 1.5 equivalents of Cy 2 NMe as a base, and 1.0 equivalent of [bmim]PF 6 in dioxane were irradiated at 180 8C under sealedvessel conditions (no inert gas atmosphere) with the aryl chloride and butyl acrylate for 30-60 min.…”

Section: Microwave Chemistrymentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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Section: Microwave Chemistrymentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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“…Quest for High TON Herrmann et al [22] have reviewed applications of metal complexes 36, 45, 52, 56, 105 and 106 ( Figure 10) in Heck type reactions where detailed information about developments in palladium catalytic systems and their successful approach towards activation of less reactive substrates like aryl chlorides is mentioned. Palladacycles are found to be active against a broad spectrum of reactions and have advantages like active towards more economic aryl halides, high activity at low palladium:ligand ratio (1:1) and improved thermal stability and life-time in solution.…”

Section: Homogeneous Catalysismentioning

confidence: 99%

Heck Reaction—State of the Art

Jagtap¹

2017

Catalysts

175

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Abstract:The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustively describing the various aspects of Heck reaction and refer to the work done hitherto. Looking at the quantum of the monographs published, and the reviews based on them, we found a necessity to summarize all reviews on Heck reaction about catalysts, ligands, suggested mechanisms, conditions, methodologies and the compounds formed via Heck reaction in one review and generate a resource of information. One can find almost all the catalysts used so far for Heck reaction in this review.

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“…Usually, cyclopalladated ligands have little effect on the catalytic activity, however, variation of the anionic ligand X(Cl, Br, I, OAc, etc.) is found to have some effect on the catalytic activity [20,21]. In order to further investigate the effect of halogen anions on the catalytic activity, we studied the Suzuki reactions catalyzed by the palladacycle adducts 2-3 containing chloride/iodide anions.…”

Section: Application In Suzuki Reactionmentioning

confidence: 99%

Synthesis and Characterization of Triphenylphosphine Adducts of Ferrocene-Based Palladacycles and Their Performance in the Suzuki and Sonogashira Reactions with Bromo- and Chloroarenes

Bai

et al. 2012

Molecules

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Abstract:A new triphenylphosphine adduct of cyclopalladated ferrocenylpyridazine containing a chloride anion, 2a, has been synthesized from the reaction of the chloride-bridged palladacyclic dimer 1a with triphenylphosphine. The corresponding adducts 3a,b containing iodide anion have been readily prepared through anion exchange reactions of 2a,b with NaI in acetone. These complexes were characterized by elemental analysis, IR and 1 H-NMR. Additionally, their crystal structures have been determined by X-ray diffraction and intermolecular C-H···X (Cl, Br, I) bonds were found in the crystals. The use of these palladacycles as catalysts for the Suzuki and Sonogashira reactions was examined. The complexes 2a,b exhibited higher catalytic activity than the corresponding 3a,b in the Suzuki reaction. However, the order of activity of adducts with varying halogen anions is 3a~3b > 2a~2b in the Sonogashira reaction.

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Application of palladacycles in Heck type reactions

Cited by 560 publications

References 103 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Heck Reaction—State of the Art

Synthesis and Characterization of Triphenylphosphine Adducts of Ferrocene-Based Palladacycles and Their Performance in the Suzuki and Sonogashira Reactions with Bromo- and Chloroarenes

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