Novel cyclometallated Pd(II) and Pt(II) complexes with indole derivatives and their use as catalysts in Heck reaction

Cravotto, Giancarlo; Demartin, Francesco; Palmisano, Giovanni; Penoni, Andrea; Radice, Tiziano; Tollari, Stefano

doi:10.1016/j.jorganchem.2004.11.042

Cited by 27 publications

(18 citation statements)

References 30 publications

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“…The bite angles of five-membered ring N indolyl -Pd-N pyridinyl or N indolyl -Pd-N oxazolinyl (78.0(2)° for 3 and 79.33(11)° for 5 ) are similar to those (81.14(12)° for N indolyl -Pd-N pyridinyl [ 12 ]; 79.89(7)° or 80.06(9)° for N imino -Pd-N pyridinyl [ 16 ]; 81.78(8)° or 81.37(11)° for N imino -Pd-N pyridinyl [ 13 , 18 ]; 81.39(12)° for N amido -Pd-N quinolinyl [ 19 ]; 81.76(6)° for N amido -Pd-N pyridinyl [ 14 ]) found in the literature. The bite angles of six-membered ring N indolyl -Pd-N pyridinyl (90.8(8)° for 3 and 89.01(11)° for 5 ) are larger than those found in five-membered ring.…”

Section: Resultsmentioning

confidence: 91%

“…This encourages us to develop palladium complexes bearing pincer ligands, which could be applied in cross coupling reactions. Owing to the success in preparation of some metal complexes containing the indole ring system reported by us [ 8 , 9 ] and other groups [ 10 , 11 , 12 ], introduction of the indole ring system into the pincer ligand precursors will be explored. In this paper, we intended to introduce the N -heterocyclic substituents, such as pyridine, pyrazole, or oxazoline as pendant functionalities into the indole ligands in different positions.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization, and Catalytic Application of Palladium Complexes Containing Indolyl-NNN-Type Ligands

Yang

et al. 2021

Molecules

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In this study, a series of N-heterocyclic indolyl ligand precursors 2-Py-Py-IndH, 2-Py-Pz-IndH, 2-Py-7-Py-IndH, 2-Py-7-Pz-IndH, and 2-Ox-7-Py-IndH (L1H-L5H) were prepared. The treatment of ligand precursors with 1 equivalent of palladium acetate affords palladium complexes 1–5. All ligand precursors and palladium complexes were characterized by NMR spectroscopy and elemental analysis. The molecular structures of complexes 3 and 5 were determined by single crystal X-ray diffraction techniques. The application of those palladium complexes 1–5 to the Suzuki reaction with aryl halide substrates was examined.

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Section: Resultsmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Catalytic Application of Palladium Complexes Containing Indolyl-NNN-Type Ligands

Yang

et al. 2021

Molecules

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“…[29,30] We carried out combined irradiation in a flow reactor, obtaining the expected biaryls in higher yields and shorter time than using sonication or microwaves separately. [30] Proceeding from our previous experience on the catalysis of Suzuki [29,30] and Heck reactions [31] we present here our recent results on reactions carried out with a very low ligandless catalyst load under MW or simultaneous US/MW irradiation.…”

Section: Introductionmentioning

confidence: 99%

Heck Reactions with Very Low Ligandless Catalyst Loads Accelerated by Microwaves or Simultaneous Microwaves/Ultrasound Irradiation

Palmisano

Bonrath²,

Boffa

et al. 2007

Adv Synth Catal

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Heck couplings were carried out ligandless in air with very low catalyst loads under microwave or simultaneous microwave/ultrasound irradiation.in the range of 0.01-0.1 mol % or palladium-oncarbon (Pd/C) 10 % in the range of 1.0-2.0 mol %, most aryl iodides and bromides gave high yields under conventional heating (120 8C) in 18 h. Microwave irradiation alone or, better still, combined with high-intensity ultrasound, strongly promotes the reaction, generally decreasing reaction times to 1 h. Electron-poor aryl chlorides such as 4-chloroacetophenone and 1-chloro-4-nitrobenzene reacted with styrene to afford high product yields in the presence of 0.25 mol % PdA C H T U N G T R E N N U N G (OAc) 2 or 2.0-3.0 mol % Pd/C. In several cases the addition of a co-catalyst, either rhodium tris(triphenylphosphine) chloride, 0.005 mol %, or a copper(I) salt (iodide or bromide), 2.0-4.0 mol %, proved very advantageous. 4-Bromo-and 4-chloroacetophenone afforded up to 15 % of oxidation products, namely the corresponding 4-halobenzoic acid and 4-styrylbenzoic acid, a drawback that was avoided by working under a nitrogen atmosphere.

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“…New cyclometallated Pd(II) or Pt(II) complexes with indole derivatives were synthesized because indole is a π‐excessive system with a hydrogen‐bond donor atom . Furthermore, in 2005, Tollari and co‐workers developed several palladacycle and platinacycle complexes juxtaposed with a pyridine and an indole system [11a] . They found that a new M―C bond could be formed between Pd and C‐3 of the indole ring if N ‐substituted indole was used; otherwise, an N–M–N coordination complex would be formed.…”

Section: Introductionmentioning

confidence: 99%

Indolylbenzimidazole‐based ligands catalyze the coupling of arylboronic acids with aryl halides

Wang

Chiu

et al. 2018

Applied Organom Chemis

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A novel class of compounds bearing indole and benzimidazole rings was designed and easily synthesized from 2-indolecarboxylic acid and ophenylenediamine.The catalytic system derived from a 2indolylbenzimidazole-based ligand and Pd(OAc) 2 in situ could lead to complete conversion of aryl bromides at 0.5 mol% Pd loading under mild reaction conditions. In the presence of a catalyst, sterically hindered biaryls were selectively generated in excellent yields by adjusting reaction parameters through the coupling of arylboronic acids with aryl halides. The efficiency of this reaction was demonstrated by its compatibility with various functional groups.

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Novel cyclometallated Pd(II) and Pt(II) complexes with indole derivatives and their use as catalysts in Heck reaction

Cited by 27 publications

References 30 publications

Synthesis, Characterization, and Catalytic Application of Palladium Complexes Containing Indolyl-NNN-Type Ligands

Synthesis, Characterization, and Catalytic Application of Palladium Complexes Containing Indolyl-NNN-Type Ligands

Heck Reactions with Very Low Ligandless Catalyst Loads Accelerated by Microwaves or Simultaneous Microwaves/Ultrasound Irradiation

Indolylbenzimidazole‐based ligands catalyze the coupling of arylboronic acids with aryl halides

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