Palladium complexes of P,P and P,S type bidentate ligands: Implication in Suzuki–Miyaura cross-coupling reaction

Saikia, Kokil; Deb, Biswajit; Borah, Bibek Jyoti; Sarmah, Podma Pollov; Dutta, Dipak Kumar

doi:10.1016/j.jorganchem.2011.10.001

Cited by 27 publications

(16 citation statements)

References 34 publications

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“…Although palladium complexes of these ligands have been synthesized in the past [25,26], their catalytic activities towards C H activation reactions have not been studied. Heterobidentate ligands like a and b tend to show hemilability at the metal centre by dissociating the weaker bond during the catalytic cycles to step up the oxidative addition [27][28][29]. In our continued efforts [30][31][32][33][34][35][36][37][38][39] different coupling reactions, herein, we report synthesis and characterization of two palladium complexes of heterobidentate P-S ligand systems, and their catalytic activity towards acylation of aryl halides with aldehydes.…”

Section: Introductionmentioning

confidence: 98%

Palladium complexes of heterobidentate ligands: Active catalysts for direct acylation of aryl halides with aldehydes via C(sp 2 )-H activation

Saikia

Dutta

2015

Journal of Molecular Catalysis A: Chemical

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Section: Introductionmentioning

confidence: 98%

Palladium complexes of heterobidentate ligands: Active catalysts for direct acylation of aryl halides with aldehydes via C(sp 2 )-H activation

Saikia

Dutta

2015

Journal of Molecular Catalysis A: Chemical

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“…POP dioxide adopts a conformation unlike (1) or (2), as the P-O bond vectors are closer to antiparallel [intramolecular OPÁ Á ÁP-O angles of 37.0 (6) ]. Considering metal complexes of related ligands, the structures of only two ruthenium(II) complexes , three palladium(II) complexes (Milheiro & Faller, 2011;Saikia et al, 2012), and one rhodium(I) complex (Faller et al, 2008) have been reported with Xantphos sulfide or POP sulfide. The structure of only one palladium(II) complex of Xantphos disulfide (Jahromi et al, 2012) is reported.…”

Section: Supramolecular Featuresmentioning

confidence: 99%

Crystal structures of bis[2-(diphenylphosphinothioyl)phenyl] ether and bis{2-[diphenyl(selanylidene)phosphanyl]phenyl} ether

2014

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2 , (2), exhibit remarkably similar structures although they are not isomorphous. The whole molecule of compound (2) is generated by twofold symmetry, with the ether O atom located on the twofold axis. Both compounds have intramolecularinteractions between terminal phenyl rings with centroid-centroid distances of 3.6214 (16) and 3.8027 (14) Å in (1) and (2), respectively. In the crystal of (1), short C-HÁ Á ÁS hydrogen bonds link the molecules, forming chains along [001], while in (2) there are no analogous C-HÁ Á ÁSe interactions present. Chemical contextThe ligand bis[2-(diphenylphosphanyl)phenyl] ether (POP) and its congeners, including the more rigid Xantphos [(9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane)], comprise a series of chelating diphosphines with a range of flexibility to accommodate variable bonding geometries at transition metals. Experimental and theoretical studies of metal complexes with diphosphines have shown a strong correlation between diphosphine bite angle and selectivity in catalytic transformations (Dierkes & van Leeuwen, 1999;Gathy et al., 2011). Simple functionalization of these diphosphines to form diphosphine dioxides, disulfides, and diselenides has permitted further tuning of the bonding of these ligands to metals by changing the bite-angle range as well as the electronic properties of these ligands. The -accepting phosphorous donor atoms of the parent diphosphines are profoundly altered with the addition of -donor chalcogen donor atoms (Dairiki et al., 2009). Chalcogen-modified diphosphine ligands have been utilized in strategies to tune the catalytic behavior of systems including the Pd II -catalysed hydroamination of dienes (Jahromi et al., 2012) and Ru II transfer hydrogenation of aldehydes and ketones . Hemilability, implicated in the selectivity and reactivity of some catalytic reactions (Braunstein et al., 2001), can also result from the chalcogen functionalization of phosphines as well .Our interest in the application of chalcogen-substituted diphosphines to alter the electronic features of photoluminescent Cu I sensor materials (Smith et al., 2010) led us to study the solid-state structural features of the dichalcogen diphosphines, including the disulfide and diselenide of the ligand POP. We wanted to investigate the inter-and intramolecular features that dominate the solid-state structural behavior of these ligands. The molecular geometry and Structural commentaryThe molecular structures of (1) and (2) (2)], the intramolecular EÁ Á ÁE distances [E = S 6.636 (1) Å for (1); E = Se 6.8246 (7) Å for (2)], and the EPÁ Á ÁPE angles [158.29 (4) for (1); 158.44 (2) for (2)] all indicate a common geometry near the phosphorous-chalcogen bonds. This similarity extends to the phenyl ring orientations. A structural overlap calculation of the pairwise atomic coordinates of all related atoms of (1) and (2) (except the chalcogens) reveals an r.m.s. deviation of only 0.214 Å over 39 atom pairs (Fig. 3).The largest differences in the intramolecular features of (1) and (2) can...

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“…In fact, this ligand has been extensively studied for various transition metal‐catalysed reactions including palladium‐catalysed cross‐coupling reactions like Negishi, Kumada–Corriu, etc . Unfortunately, the potentiality of this ligand in the Suzuki–Miyaura cross‐coupling reaction is virtually unexplored, although other related bulky diphosphines have shown promising cross‐coupling activity [4c,9a,12] …”

Section: Introductionmentioning

confidence: 99%

Palladium complex containing two sterically hindered ligands as highly efficient catalyst for Suzuki–Miyaura reaction

Shahnaz

Das

2015

Applied Organom Chemis

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A new palladium(II) complex containing two sterically hindered ligands, a P,P-bonded diphosphine and N,N-bonded Schiff base, within the same coordination sphere has been synthesized and investigated as a catalyst for the Suzuki-Miyaura crosscoupling reactions of aryl halides with arylboronic acids. The reaction was highly efficient with aryl bromides in water at room temperature and aryl chlorides in dimethylformamide under relatively mild conditions. Excellent yields of coupling products were obtained for a wide range of aryl halides including heteroaryl halides with a low loading of catalyst. Figure 2. Effect of base and solvent on the conversion of 4chloronitrobenzene (reaction conditions: 4-chloronitrobenzene (0.5 mmol), phenylboronic acid (0.75 mmol), base (1.5 mmol), complex 2 (1 mol%), solvent (4 ml), 80°C, 5 h).

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Palladium complexes of P,P and P,S type bidentate ligands: Implication in Suzuki–Miyaura cross-coupling reaction

Cited by 27 publications

References 34 publications

Palladium complexes of heterobidentate ligands: Active catalysts for direct acylation of aryl halides with aldehydes via C(sp 2 )-H activation

Palladium complexes of heterobidentate ligands: Active catalysts for direct acylation of aryl halides with aldehydes via C(sp 2 )-H activation

Crystal structures of bis[2-(diphenylphosphinothioyl)phenyl] ether and bis{2-[diphenyl(selanylidene)phosphanyl]phenyl} ether

Palladium complex containing two sterically hindered ligands as highly efficient catalyst for Suzuki–Miyaura reaction

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