Isolation of chloro-bridged arylpalladium complexes, [Pd2Ar2(μ-Cl)2(PR3)2], in palladium catalyzed C–C cross coupling reaction of triarylbismuth with arylhalides

Chaudhari, Kamal R.; Wadawale, Amey; Jain, Vimal K.

doi:10.1016/j.jorganchem.2011.09.024

Cited by 30 publications

(8 citation statements)

References 45 publications

(35 reference statements)

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“…The other two neopentyl substituents adopt pseudogauche conformations relative to the Pd–P bond and are positioned above and below the Pd 2 Br 2 plane. The trineopentylphosphine conformation is similar to that seen in [(Et 3 P)Pd(4-tolyl)Cl] 2 ( 4 ) …”

Section: Resultssupporting

confidence: 57%

“… a Measurements taken from planar dimeric structure (Figure ). b [(Et 3 P)Pd(4-tolyl)Cl] 2 c Chloride in place of bromide. d % V b calculated using the SambVca 2.0 Web application …”

Section: Resultsmentioning

confidence: 99%

“…The trineopentylphosphine conformation is similar to that seen in [(Et 3 P)Pd(4-tolyl)Cl] 2 (4). 15 The conformation of the PNp 3 ligand in the [(PNp 3 )-PdArBr] 2 complexes is affected by the presence of orthosubstituents on the aryl ligand (Figure 3). When the aryl group has no ortho substituents (3a and 3b), the PNp 3 ligand adopts a conformation with pseudomirror plane symmetry in which one neopentyl substituent (C1) is nearly eclipsed with the Pd− C Ar bond (C1−P−Pd−C Ar = 4.93 (3a), 6.94 (3b); Table 1) and has an anti relationship to the Pd−P bond (Pd−P−C1−C 177−180°).…”

Section: Structural Comparison Of Solid Statementioning

confidence: 99%

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Synthesis, Structural Characterization, and Coordination Chemistry of (Trineopentylphosphine)palladium(aryl)bromide Dimer Complexes ([(Np₃P)Pd(Ar)Br]₂)

Vasiliu

Stein

et al. 2019

Inorg. Chem.

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A series of [(PNp 3 )Pd(Ar)Br] 2 complexes (PNp 3 = trineopentylphosphine, and 2, were synthesized and structurally characterized by X-ray crystallography and density functional theory optimized structures. The trineopentylphosphine ligand is able to accommodate coordination of other sterically demanding ligands through changes in its conformation. These conformational changes can be seen in changes in percent buried volume of the PNp 3 ligand. The binding equilibria of the [(PNp 3 )Pd(Ar)Br] 2 complexes with pyridine derivatives were determined experimentally and analyzed computationally. The binding equilibria are sensitive to the steric demand of the pyridine ligand and less sensitive to the steric demand of the aryl ligand on palladium. In contrast to previous studies, the binding equilibria do not correlate with pyridine basicity. The binding equilibria results are relevant to fundamental ligand coordination steps in cross-coupling reactions, such as Buchwald−Hartwig aminations.

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Section: Resultssupporting

confidence: 57%

“… a Measurements taken from planar dimeric structure (Figure ). b [(Et 3 P)Pd(4-tolyl)Cl] 2 c Chloride in place of bromide. d % V b calculated using the SambVca 2.0 Web application …”

Section: Resultsmentioning

confidence: 99%

Section: Structural Comparison Of Solid Statementioning

confidence: 99%

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Synthesis, Structural Characterization, and Coordination Chemistry of (Trineopentylphosphine)palladium(aryl)bromide Dimer Complexes ([(Np₃P)Pd(Ar)Br]₂)

Vasiliu

Stein

et al. 2019

Inorg. Chem.

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“…Shortly after these reports, Rao published similar protocols to cross-couple triarylbismuthines with bromopyridines and quinolines (Scheme 39 B). 239 Other catalytic systems have been used to promote cross-coupling reactions between organobismuth reagents and various electrophiles such as a reusable polystyreneresin-supported palladium catalyst, 240 palladium-on-carbon, 241 chloro-bridged arylpalladium complexes, 242 palladium(II) chalcogenolate complexes, 243 an MCM-41-immobilized palladium(II)-Schiff base complex [MCM-41-2N-Pd(OAc) 2 ] 244 and PEPPSI. 245 Resin-bound bromotriarylbis-muthine reagents have also been developed to perform solid-phase cross-coupling reactions with arylboronic acids.…”

Section: Cross-coupling With Aryl and Heteroaryl Halides And Pseudo Hmentioning

confidence: 99%

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

2017

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Organobismuth compounds are organometallic reagents that contain a C-Bi bond. These species, which are easily accessed from inexpensive and low-toxicity inorganic bismuth salts, are highly attractive in synthesis due to their unique properties and reactivity. A wide diversity of geometries have been found for organobismuth compounds, depending on the oxidation state of the bismuth, its charge, and the number of coordinated elements. Compounds where the bismuth bears a-1 charge (organobismuthate), a +1 (bismuthonium cation) and a +2 charge (bismuthonium dication) have been reported. Due to the presence of a lone pair, trivalent organobismuthines can act as Lewis bases in transition-metal complexes. In addition, organobismuth compounds can act as Lewis acids by forming hypervalent interactions with ligands and metals. Organobismuth compounds have been used as catalysts and reagents in a plethora of reactions. In this review, the synthesis and properties of organobismuth reagents and their use in organic reactions are reviewed. 1 Introduction 2 Synthesis of Trivalent Organobismuthines 3 Synthesis of Pentavalent Organobismuth Compounds 4 Structure, Hypervalency and Chirality 5 C-, N-, Oand S-Arylation Reactions 6 Palladium-Catalyzed Reactions 7 Other Reactions Involving Organobismuth Reagents 8 Conclusion

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“…One of the most important chemists’ achievements is the discovery of the carbon–carbon coupling reactions in the presence of a complex containing transition metal such as copper, palladium, nickel, and iron. Among transition metals complexes, palladium is one of the best choices, due to its simple complex preparation, high activity, and selectivity in coupling reactions 19 – 24 . In organic chemistry science, a variety of coupling reaction systems has been discovered, designed, and introduced: Heck reaction 25 , Suzuki reaction 26 , Negishi reaction 27 , Stille reaction 28 , Sonogashira reaction 25 , Kumada coupling 26 , Hiyama coupling reaction 27 , and Buchwald–Hartwig reaction 29 .…”

Section: Introductionmentioning

confidence: 99%

Design and synthesis of Fe3O4@SiO2@KIT-6@DTZ-Pd0 as a new and efficient mesoporous magnetic catalyst in carbon–carbon cross-coupling reactions

Moradi

Ghorbani‐Choghamarani

2021

Sci Rep

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In this paper, a new type of mesoporous material based on KIT-6 has been introduced. In this aim, magnetic Fe3O4 nanoparticles and mesoporous silica KIT-6 have been combined to obtain mesoporous MNPs. The prepared magnetic mesoporous catalyst has been applied in different carbon–carbon cross-coupling reactions including Mizoroki–Heck, Suzuki–Miyaura, and Stille reactions. This magnetic mesoporous compound is characterized by various techniques including FT-IR, BET, VSM, SEM, XRD, and TGA.

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Isolation of chloro-bridged arylpalladium complexes, [Pd2Ar2(μ-Cl)2(PR3)2], in palladium catalyzed C–C cross coupling reaction of triarylbismuth with arylhalides

Cited by 30 publications

References 45 publications

Synthesis, Structural Characterization, and Coordination Chemistry of (Trineopentylphosphine)palladium(aryl)bromide Dimer Complexes ([(Np₃P)Pd(Ar)Br]₂)

Synthesis, Structural Characterization, and Coordination Chemistry of (Trineopentylphosphine)palladium(aryl)bromide Dimer Complexes ([(Np₃P)Pd(Ar)Br]₂)

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

Design and synthesis of Fe3O4@SiO2@KIT-6@DTZ-Pd0 as a new and efficient mesoporous magnetic catalyst in carbon–carbon cross-coupling reactions

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Isolation of chloro-bridged arylpalladium complexes, [Pd2Ar2(μ-Cl)2(PR3)2], in palladium catalyzed C–C cross coupling reaction of triarylbismuth with arylhalides

Cited by 30 publications

References 45 publications

Synthesis, Structural Characterization, and Coordination Chemistry of (Trineopentylphosphine)palladium(aryl)bromide Dimer Complexes ([(Np3P)Pd(Ar)Br]2)

Synthesis, Structural Characterization, and Coordination Chemistry of (Trineopentylphosphine)palladium(aryl)bromide Dimer Complexes ([(Np3P)Pd(Ar)Br]2)

Organobismuth Reagents: Synthesis, Properties and Applications in Organic Synthesis

Design and synthesis of Fe3O4@SiO2@KIT-6@DTZ-Pd0 as a new and efficient mesoporous magnetic catalyst in carbon–carbon cross-coupling reactions

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Product

Resources

About

Synthesis, Structural Characterization, and Coordination Chemistry of (Trineopentylphosphine)palladium(aryl)bromide Dimer Complexes ([(Np₃P)Pd(Ar)Br]₂)

Synthesis, Structural Characterization, and Coordination Chemistry of (Trineopentylphosphine)palladium(aryl)bromide Dimer Complexes ([(Np₃P)Pd(Ar)Br]₂)