Organotrifluoroborates and Monocoordinated Palladium Complexes as Catalysts—A Perfect Combination for Suzuki–Miyaura Coupling

Molander, Gary A.; Canturk, Belgin

doi:10.1002/anie.200904306

Cited by 411 publications

(183 citation statements)

References 183 publications

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“…However, tetra-coordinated organoborates have gained increased popularity due to their ready availability and ease of handling. 5,[38][39][40][41][42] Especially organotrifluoroborates offer substantial benefits. They are air and moisture stable and can be easily prepared and purified; 5,43 however their use as substrates in Suzuki reactions is only marginally exploited.…”

Section: Introductionmentioning

confidence: 99%

Suzuki cross-coupling in aqueous media

et al. 2015

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We report a simple and efficient procedure for the ligand-free as well as ligand-assisted Suzuki reaction in both pure water and aqueous media. The cross-coupling reactions proceed successfully using phenylboronic acid or potassium phenyltrifluoroborate as a nucleophilic coupling partner. The method can be effectively applied to both activated and deactivated aryl halides yielding quantitative conversions. The catalytic activity of couplings performed in pure water increases when utilizing supramolecular additives, but decreases under standard phase-transfer conditions. Finally, the palladium loading is reducible from 3.0 mol% to 0.4 mol% without any loss of conversion.

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Section: Introductionmentioning

confidence: 99%

Suzuki cross-coupling in aqueous media

et al. 2015

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“…In Suzuki reactions, the activity of the catalyst depends on the nature of the ligand attached to the Pd metal [8]. Bulky electron-rich phosphine ligands are prominent in the palladium-catalyzed Suzuki cross-coupling reaction, due to their superior donor capability and stabilization effects [9][10][11][12]. In recent years, various palladium-phosphine catalysts have been developed for efficient cross-coupling reactions [13][14][15][16][17][18][19][20], but most of the known systems give sub-optimal results for the Suzuki coupling of less reactive aryl halides.…”

Section: Introductionmentioning

confidence: 99%

A palladium–phosphine catalytic system as an active and recycable precatalyst for Suzuki coupling in water

Sabounchei

Hosseinzadeh

Panahimehr

et al. 2015

Transition Met Chem

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The Suzuki-Miyaura reaction of various aryl halides with aryl boronic acids using {[Ph 2 PCH 2 PPh 2-CH=C(O)(C 10 H 7 )]PdCl 2 } as a catalyst has been investigated. The X-ray crystal structure of the catalyst reveals a five-membered chelate ring formed by coordination of the ligand through the phosphine group and the ylidic carbon atom to the metal center. This palladacycle exhibited excellent activities and reusability in the aqueous phase for the Suzuki cross-coupling reactions of arylboronic acids with aryl halides. The proposed protocol featured mild reaction conditions and notable simplicity and efficiency using Cs 2 CO 3 as a base in water. The catalytic system could be reused four times without significant loss of activity.

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“…For example, the reaction has attracted the interest of several research teams involved in high-throughput chemistry, as a large variety of boronic acids are commercially available [12]. As alternatives to the less reactive boronic ester derivatives, the recent emergence of more stable organotrifluoroborates [24] and N-methyliminoacetic acid (MIDA) boronates [25] has further increased the utility of the Suzuki reaction. In addition, a high-speed synthesis of aryl boronates (Suzuki coupling reactants) has been carried out under single-mode irradiation with an in situ-generated palladium carbene catalyst [26].…”

Section: The Suzuki-miyaura Reactionmentioning

confidence: 99%