A Lutidine‐Bridged Bis‐Perimidinium Salt: Synthesis and Application as a Precursor in Palladium‐Catalyzed Cross‐Coupling Reactions

Tu, Tao; Malineni, Jagadeesh; Bao, Xiaoling; Dötz, Karl Heinz

doi:10.1002/adsc.200800768

Cited by 70 publications

(33 citation statements)

References 49 publications

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“…Thus, the use of microwave irradiation shortens the reaction time significantly at nearly the same temperature as compared with literature data. 23,24,26 If we consider the difficulties in producing perimidine derivatives and the short reaction time, the achieved yields are quite satisfactory. Elemental analysis data are in unison with the structures of compounds 2a-e.…”

mentioning

confidence: 86%

“…Also in the case of the Suzuki reaction only Tu and co-workers have reported the use of perimidinium/Pd (OAc) 2 catalytic system. 23 They carried out the reaction of phenylboronic acid with iodobenzene or bromobenzene and obtained good yields (49-95%) at low catalyst loading.…”

mentioning

confidence: 99%

“…The use of Pd(OAc) 2 -perimidinium salt catalytic system in this reaction is reported only by Tu and co-workers, and this study is an isolated instance in literature. 23 They carried out the Heck reaction with n-butyl acrylate and aryl halides and obtained the products in good Chemistry of Heterocyclic Compounds 2015, 51(6), 563-567 The effect of the reaction time was tested in the reaction of 4-bromobenzaldehyde and styrene using Pd(OAc) 2 /2d catalytic system and Cs 2 CO 3 as a base (Table 1, entries 18, 21). As seen from Table 1, we did not obtain noteworthy yield of the desired product in 30 min (entry 21).…”

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confidence: 99%

“…Perimidine-based NHCs and its Rh complexes were investigated first time in 2003 by Richeson and coworkers 20 but only a few perimidine-based catalysts have been reported in literature so far by the other research groups. [21][22][23][24][25][26] In addition to catalytic applications of perimidine derivatives, their anti-inflammatory, 27 antioxidant, 28 antimicrobial, 29 antibacterial, 30 antitumor, 31 and dyestuff 32 properties were reported.…”

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confidence: 99%

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Microwave-Assisted Synthesis of Novel Perimidinium Salts as N-Heterocyclic Carbene Precursors: Involvement in Palladium-Catalyzed Cross-Coupling Reactions

Onar

Karataş

Alıcı

et al. 2015

Chem Heterocycl Comp

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confidence: 86%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Microwave-Assisted Synthesis of Novel Perimidinium Salts as N-Heterocyclic Carbene Precursors: Involvement in Palladium-Catalyzed Cross-Coupling Reactions

Onar

Karataş

Alıcı

et al. 2015

Chem Heterocycl Comp

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“…Indeed, the bis(perimidinium) salt 213 (Chart 23) was synthesized in quantitative yield from readily available starting materials, and it has been employed in combination with palladium acetate as efficient precatalyst for reaction of iodo-and bromoarenes with n-butyl acrylate. 68 The ·-donor ability of NHC ligand generated from bis(perimidinium) salt is higher than the analogous NHC ligands starting from bis(imidazolium) and bis(benzimidazolium) that improves the efficiency of the palladium catalyst formed in situ. The reaction of 4-bromotoluene produced the expected product with 77% yield employing 0.0002 mol % of palladium (with a TON of 385000).…”

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confidence: 99%

Heterocyclic Carbene–Metal-catalyzed Csp2–Csp2 and Csp–Csp2 Couplings Using Nonmetallic Substrates

Yus¹,

Pastor²

2013

Chemistry Letters

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The use of carbene ligands for transition-metal complexes has been developed in the last decades, being of special interest those carbenes derived from a nitrogen-containing heterocyclic system. An interesting variety of carbenemetal complexes has been tested in the MizorokiHeck reaction. In comparison, few examples can be found for the MatsudaHeck version of this coupling reaction. Additionally, the Sonogashira coupling has been also catalyzed with different carbenemetal catalysts. Ç IntroductionN-Heterocyclic carbenes (NHCs) have emerged in the last years as a new family of ligands with interesting electronic and structural properties.1 The combination of their strong ·-donor and poor ³-acceptor abilities results in good coordination stability and versatility. Consequently, the use of NHC ligands based on imidazolium ions and related heterocycles has appeared as an alternative to phosphanes in the design of new organometallic catalysts.2 One of the main advantages of employing NHC-based catalysts compared with phosphanebased ones is that they are far less prone to oxidation, allowing their prolonged use, and reuse. Although NHCs were presented as simple tertiary phophane mimics, they have been recognized as much more over the past decade. Therefore, NHC ligands have become an interesting alternative to other types of ligands in different cross-coupling catalytic reactions mediated by transition metals.3 Moreover, the easy introduction of chiral elements in the corresponding precursors have made chiral NHCs promising chiral ligands in metal-based asymmetric catalysis. 4 The comparison between phosphane and NHC ligands, from a mechanistic point of view, has been studied, clear differences being found.5 First, the possibility of carbene ligand dissociation is greatly reduced due to its stronger donor ability; and second, the reactivity of the NHCmetal complex is higher probably caused by the lack of back-donation from the metal to the carbene ligand. Jutand and co-workers studied the reactivity of monocarbene and bis(carbene) Pd(0) complexes toward the oxidative addition of aryl halides, concluding that the electronic and steric properties of the carbene ligand are important factors in this step of the catalytic process. 6 Among the carboncarbon coupling reactions, the activation of a CH from an alkene (MizorokiHeck reaction) or an alkyne (Sonogashira reaction) are of special interest. This highlight review describes the progress on the topic of NHC ligands for transition-metal-catalyzed coupling reactions, employing nonmetallic reagents. Thus, both different NHC precursors and NHCmetal complexes with catalytic activity in the Mizoroki Heck, MatsudaHeck, and Sonogashira reactions are compiled. Ç Mizoroki-Heck ReactionIn 1995, Herrmann and co-workers introduced the use of bis(NHC)Pd complexes as catalysts with long-term stability in the MizorokiHeck reaction.7 Indeed, the carbenes derived from imidazole stabilized the palladium complexes due to their pronounced donor properties, being more stable toward...

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Recent Advances in Palladium‐Catalyzed Cross‐Coupling Reactions at ppm to ppb Molar Catalyst Loadings

2017

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We review here new developments in decreasing the catalyst loadings in palladium-catalyzed C-C bond-formation reactions to mol ppm or mol ppb levels.T his decreasest he cost of the catalyst and the toxicity of the reactions ystem, making the reactionm ore attractive to industry.T he Heck reaction, Sonogashira reaction, Suzuki-Miyaurac rosscoupling reaction, other cross-coupling reactions,a nd allylic arylation reactions are separately discussedt o show clearly the progress made in each type of reaction. Apart from the catalyst loading, the other parameters of the reaction( temperature,s olvent, etc.) are brieflyd iscussed to illustrate the shift toward greenerc onditions.F or most reactions,t his shift is underway or wella dvanced, andc atalyst loadings have been decreasedt ob elow 1mol ppm. An abundance of catalytic systems are now available,a nd it is sometimes difficult to identify the best one,b ecause the substratese xamined can vary widely from publication to publication.I nt he future,e mphasis should be placed on the studyingt he full scope of the reaction at mol ppm catalyst loadings,r athert han examining af ew examples at these levels during the reaction-optimization process.1I ntroduction 2M izoroki-Heck Coupling 3S onogashira Coupling 4S uzuki-MiyauraCross-Coupling 5O ther Cross-Coupling Reactions 6A llylic Arylation 7C onclusions

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A Lutidine‐Bridged Bis‐Perimidinium Salt: Synthesis and Application as a Precursor in Palladium‐Catalyzed Cross‐Coupling Reactions

Cited by 70 publications

References 49 publications

Microwave-Assisted Synthesis of Novel Perimidinium Salts as N-Heterocyclic Carbene Precursors: Involvement in Palladium-Catalyzed Cross-Coupling Reactions

Microwave-Assisted Synthesis of Novel Perimidinium Salts as N-Heterocyclic Carbene Precursors: Involvement in Palladium-Catalyzed Cross-Coupling Reactions

Heterocyclic Carbene–Metal-catalyzed Csp2–Csp2 and Csp–Csp2 Couplings Using Nonmetallic Substrates

Recent Advances in Palladium‐Catalyzed Cross‐Coupling Reactions at ppm to ppb Molar Catalyst Loadings

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