Sulfur-Containing Palladacycles:  Efficient Phosphine-Free Catalyst Precursors for the Suzuki Cross-Coupling Reaction at Room Temperature

Zim, Danilo; Gruber, Adriane S.; Ebeling, Günter; Dupont, Jaı̈rton; Monteiro, Adriano L.

doi:10.1021/ol0063048

Cited by 227 publications

(101 citation statements)

References 25 publications

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“…[24] Other P,C-palladacycles have been described, [43,120,121] as well as the novel C,S-palladacycles, [122,123] and even C,N,N-palladacycles. [124] These catalysts perform relatively well in simple systems, and it is not worth discussing them in further detail here, as their behavior resembles that of the many other palladacycles already discussed.…”

Section: Reviewsmentioning

confidence: 99%

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

2004

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This review discusses the problems associated with developing high-turnover catalysts for the cross-coupling and Heck reactions. New developments in the area, principally constituted by palladacycles and coordinatively unsaturated Pd catalysts featuring bulky phosphanes of high donicity, are reviewed from a mechanistic and synthetic standpoint, and compared with more traditional catalysts obtained from conventional mono-and polydentate Nand P-based ligands, as well as Pd catalysts without strong ligands, such as Pd colloids or heterogeneous catalysts. Carbene ligands are also briefly presented. Whereas a single, most promising approach to highturnover Pd catalysis cannot presently be defined, it is clear that the new "PdL 1 " catalysts (where L 1 is a monodentate bulky P ligand of high donicity) represent the latest, most important development in Pd research, certainly from the standpoint of scope and probably also from the standpoint of efficiency. High turnovers with these catalysts have been described and their use will certainly increase in the next few years. The review ends with a brief discussion containing practical considerations on how to choose a high TON catalyst for a given Heck or cross-coupling reaction of interest.

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Section: Reviewsmentioning

confidence: 99%

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

2004

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“…In addition, long reaction times are usually required. Impressive progress in the development of efficient catalytic systems to achieve this reaction under mild conditions has been made in the last several years, [3,4] but there still exists considerable room for further exploration, as only a few methods for palladiumcatalyzed Suzuki-Miyaura coupling at room temperature without the aid of any ligands have been developed. [5][6][7] Among those ligand-free and room temperature SuzukiMiyaura coupling transformations, many methods have still required other additional promoters, [5] such as phase-trans-perature in EtOH as the solvent.…”

Section: Introductionmentioning

confidence: 99%

Mild and Ligand‐Free Palladium‐Catalyzed Cross‐Couplings between Aryl Halides and Arylboronic Acids for the Synthesis of Biaryls and Heterocycle‐Containing Biaryls

et al. 2007

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Ligand‐free palladium‐catalyzed Suzuki–Miyaura cross‐couplings between aryl halides and arylboronic acids performed at room temperature are presented. It was found that both solvent and base had a fundamental influence on the reaction, and the most effective system in terms of yield and rate was observed to be the combination of Pd(OAc)2 with MeONa and alcohols. In the presence of Pd(OAc)2 and MeONa, a variety of aryl halides reacted very rapidly with arylboronic acids in good to excellent yields at room temperature in EtOH as the solvent. Moreover, the Pd(OAc)2/MeONa catalytic system could also be applied in couplings between heteroaryl halides and arylboronic acids to provide satisfactory results in MeOH as the solvent after prolonged reaction times. It is noteworthy that the reactions were conducted under mild, aerobic, and ligand‐free conditions.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…39～41 ℃ (lit. [56] m.p. After the first run of the coupling reaction between bromobenzene and phenylboronic acid, the catalyst was isolated by filtration, and washed with water (10 mL×3) and dichloromethane (10 mL×3) sequentially.…”

Section: Characterizationsmentioning

confidence: 99%

C-C Coupling Reactions in Water Catalyzed by Palladium

Kong¹,

Malik²,

Qian³

et al. 2018

Chin. J. Org. Chem.

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Sulfur-Containing Palladacycles: Efficient Phosphine-Free Catalyst Precursors for the Suzuki Cross-Coupling Reaction at Room Temperature

Cited by 227 publications

References 25 publications

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

High‐Turnover Palladium Catalysts in Cross‐Coupling and Heck Chemistry: A Critical Overview

Mild and Ligand‐Free Palladium‐Catalyzed Cross‐Couplings between Aryl Halides and Arylboronic Acids for the Synthesis of Biaryls and Heterocycle‐Containing Biaryls

C-C Coupling Reactions in Water Catalyzed by Palladium

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