Palladium(<scp>ii</scp>)-selenated Schiff base complex catalyzed Suzuki–Miyaura coupling: Dependence of efficiency on alkyl chain length of ligand

Rao, Gyandshwar Kumar; Kumar, Arun; Kumar, Bharat; Kumar, Dinesh; Singh, Ajai K.

doi:10.1039/c1dt11695a

Cited by 91 publications

(75 citation statements)

References 82 publications

(1 reference statement)

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“…The Pd–S bond length in 1 [2.269(2) Å] is consistent with previously reported values [2.254(4)–2.288(12) Å] 12g,12h,12j. The Pd–N bond lengths of 1 and 2 are within the range [1.999(6)–2.057(2) Å] for such bonds in several previously reported species 12a,12e. The Pd–O bond length in 2 [1.9787(18) Å] is consistent with the value [2.000(5) Å] reported for a Pd II selenated Schiff base complex 12a.…”

Section: Resultssupporting

confidence: 90%

Catalytic Synthesis of Bi‐ and Teraryls in Aqueous Medium with Palladium(II) Complexes of 2‐(Pyridine‐2‐ylmethylsulfanyl)benzoic Acid

et al. 2014

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Suzuki-Miyaura coupling reactions of phenylboronic and 1,4-phenylenediboronic acid with ArBr to form bi-and teraryls have been efficiently catalyzed by the air-and moisture-insensitive complexes [PdCl 2 L1] [1, L1 = 2-(pyridine-2-ylmethyl)sulfanylbenzoic acid; 0.05-0.5 mol-%] and [Pd(L2-H) 2 ] (2, L2-H = 2-pyridin-2-yl-benzo[b]thiophen-3-ol; 0.01-0.5 mol-%). The complexes were formed by the reaction of [Pd(CH 3 CN) 2 Cl 2 ] with L1, and the catalysis proceeds in water for 1. The loading of 0.1-0.5 mol-% of Pd is very promising for the coupling reactions to form teraryls. The COOH group imparts solubility to 1 in water. Ligand L2 is formed by the unprecedented cyclization of L1 in the course of the complexation reaction. The yield of 2 increases with the reac-Biaryl compounds are important for pharmaceuticals, agrochemicals, natural products, and functional materials. [1][2][3][4] Teraryls have attracted attention owing to their presence as structural units in natural products. In materials science, chemical sensing, and some biological activity, the potential role of teraryls has been recognized. [5][6][7] Palladium-catalyzed C-C Suzuki-Miyaura coupling reactions [8] are very important synthetic tools for the synthesis of biand teraryls. Various Pd II complexes of nitrogen, [9] phosphorus, [10] N-heterocyclic carbene (NHC), [11] and chalcogen [12] ligands have been employed for such couplings. To develop the best catalytic system for Suzuki-Miyaura coupling reactions, separation, air and moisture insensitivity, recyclability, required loading, and the environmental friendliness of the catalyst are some of the strategic aspects. The use of environmentally friendly water as a solvent for the Suzuki-Miyaura coupling [13] is of great interest because it is not only safe, nontoxic, inexpensive, and plentiful [14] [a]

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Section: Resultssupporting

confidence: 90%

Catalytic Synthesis of Bi‐ and Teraryls in Aqueous Medium with Palladium(II) Complexes of 2‐(Pyridine‐2‐ylmethylsulfanyl)benzoic Acid

et al. 2014

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“…It is worth mentioning that the use of a catalyst is one of the prominent advances of aqueous‐phase systems. Our catalysts are more active than those reported in the literature in Suzuki cross‐coupling reactions …”

Section: Resultsmentioning

confidence: 84%

“…To date, ligands bearing chains of different lengths have been prepared, and the effect of the chain length was examined in palladium‐catalysed Suzuki cross‐coupling reactions . All the complexes 2a – d were observed to produce good yields in the coupling of 4‐chloroacetophenone, 4‐chloroanisole and 4‐chlorotoluene with phenylboronic acid in IPA–water mixture (1:1) (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Palladium(II) complexes bearing N‐alkylpiperidoimidazolin‐2‐ylidene derivatives: Effect of alkyl chain length of ligands on catalytic activity

Çakır

Türkmen

2017

Applied Organom Chemis

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A series of piperidoimidazolinium salts which differ in the chain lengths (butyl, octyl, dodecyl, octadecyl) and their Pd-N-heterocyclic carbene complexes with pyridine were synthesized and characterized using elemental analysis and spectroscopic methods. The effects of these ligands on catalyst activation and the performance of the complexes were studied in Suzuki-Miyaura reactions of arylboronic acid with aryl chlorides. The complex with the ligand having the longest chain length was found to be most active. The results demonstrated that the length of the alkyl chain of the piperidoimidazolin-2-ylidene controlled the dispersion and composition of the nanoparticles and it affected the catalytic activity. The impact of alkyl chain length of piperidoimidazolin-2-ylidene on the Suzuki-Miyaura reactions of arylboronic acid with aryl halides was systematically investigated.

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“…However, with high catalyst loading 0.5 mol% only such conversions were realized earlier. 23 The catalytic activity of tellurium analogue, 4 which differs from 3 only in type of chalcogen donor site is significantly lower (table 3) than that of 3. This may probably be attributed to the large size and metallic character of Te.…”

Section: Catalytic Suzuki Reactionsmentioning

confidence: 93%

Chalcogenated Schiff bases: Complexation with palladium(II) and Suzuki coupling reactions

et al. 2012

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Chalcogenated Schiff bases of 5-chloroisatin (L1-L3), 2-(methythio)benzaldehyde (L4), 2-acetylpyridine (L5) and benzaldehyde (L6-L7) have been synthesized. Both the carbonyl groups of 5chloroisatin appear to be reactive (noticed for the first time) for making >C=N bond, of course one at a time only. The 1 H, 13 C{ 1 H}, 77 Se{ 1 H} and 125 Te{ 1 H} NMR spectroscopy have been used to establish the coexistence of two products, which were found in the ratio 53:47 (E = S), 55:45 (E = Se) and 81:19 (E = Te). The larger amount is of the one in which C=O group away from NH is derivatized. The two products are not separable. Palladium complexes (1-4) of Schiff bases of other three aldehydes were synthesized. The ligands as well as complexes were characterized by multinuclear NMR spectroscopy. The crystal structures of [Pd(L4/L5)Cl][ClO 4 ] (1/2) have been solved. The Pd-Se bond lengths are 2.4172(17) and 2.3675(4) Å, respectively for 1 and 2. The Pd-complexes (3-4) of L6-L7 were explored for Suzuki-Miyaura coupling and found promising as 0.006 mol % of 3 is sufficient to obtain good conversion with TON up to 1.58 × 10 4 .

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Palladium(ii)-selenated Schiff base complex catalyzed Suzuki–Miyaura coupling: Dependence of efficiency on alkyl chain length of ligand

Cited by 91 publications

References 82 publications

Catalytic Synthesis of Bi‐ and Teraryls in Aqueous Medium with Palladium(II) Complexes of 2‐(Pyridine‐2‐ylmethylsulfanyl)benzoic Acid

Catalytic Synthesis of Bi‐ and Teraryls in Aqueous Medium with Palladium(II) Complexes of 2‐(Pyridine‐2‐ylmethylsulfanyl)benzoic Acid

Palladium(II) complexes bearing N‐alkylpiperidoimidazolin‐2‐ylidene derivatives: Effect of alkyl chain length of ligands on catalytic activity

Chalcogenated Schiff bases: Complexation with palladium(II) and Suzuki coupling reactions

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