Homocoupling of arylboronic acids catalyzed by simple gold salts

Matsuda, Takanori; Asai, Toru; Shiose, Shigeru; Kato, K.

doi:10.1016/j.tetlet.2011.07.030

Cited by 33 publications

(14 citation statements)

References 54 publications

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“…Au III has also been able to form carbon−carbon bonds by oxidative coupling of vinyl groups in vinyl gold intermediates . In addition, simple gold‐containing salts such as AuCl and NaAuCl 4 have also reported to be active in the homocoupling of phenylboronic acids . Recently a photochemical, visible‐light‐induced Suzuki type coupling of arylboronic acid and aryldiazonium salts was developed .…”

Section: Resultssupporting

confidence: 90%

“…It has been reported that simple Au chloride salts are active catalysts for this reaction. In addition many studies show that metallic Au nanoparticles, even after additional treatment with NaBH 4 to remove any cationic species, can still be active catalysts, especially if dispersed on basic support materials . Owing to the similar activity levels displayed by the HAuCl 4 and the 1 % Au/C (AR) catalyst, the latter of which is known to consist of supported Au–Cl species in the fresh catalyst, we further investigated the stability of our catalyst .…”

Section: Resultsmentioning

confidence: 99%

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Homocoupling of Phenylboronic Acid using Atomically Dispersed Gold on Carbon Catalysts: Catalyst Evolution Before Reaction

et al. 2018

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Coupling reactions to form new C−C bonds are extensively used in industrial synthetic processes. Gold has been shown to be an active catalyst for such reactions; however, conflicting reports exist as to whether cationic Au or metallic Au acts as the active species. We prepared a heterogeneous catalyst consisting of atomically dispersed Au–Clx supported on carbon and showed this to be active in the homocoupling of phenylboronic acid to biphenyl. However; characterisation of the catalyst materials, even after just a short exposure time to the reactants, revealed rapid reduction and sintering of the Au species into larger metallic nanoparticles, which we propose to be the true active species in this instance. This study suggests that if cationic Au is an active catalyst, it must be stabilised against reduction and agglomeration by either forming complexes which are more stable than common chlorides or by strongly anchoring them firmly onto alternative support materials; as in this case the carbon supported Au–Cl species were easily reduced.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Homocoupling of Phenylboronic Acid using Atomically Dispersed Gold on Carbon Catalysts: Catalyst Evolution Before Reaction

et al. 2018

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“…It proceeded smoothly in a solvent comprising DMA and THF (volume ratio is 1:1) with a yield of 77% (Table 1, entry 12). Finally, we varied the composition of DMA and THF in the range of 9:1 to 1:9 (Table 1, entries [13][14][15][16][17][18][19][20]. In general, an increase of DMA favoured the formation of biphenyl and the volume ratio of 4:1 was the best (Table 1, entry 14).…”

Section: Resultsmentioning

confidence: 99%

The Homocoupling of Arylsulfonylhydrazides by Palladium-Catalysed Desulfonation in Air

Zhang

Zhao

2013

Journal of Chemical Research

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“…These coupling partners can be classified according to different types of bond cleavage. Homocoupling of arylmetal reagents and dimerization of organoborane reagents can be achieved under oxidative Pd‐catalyzed coupling conditions (Scheme , C─M cleavage). Self‐coupling of arenediazonium salts has been well established for a long time and arylhydrazines have been recognized as alternative coupling partners recently (Scheme , C─N cleavage), while the instability of arenediazonium salts and the toxicity of arylhydrazine substrates obviously restrict the application of these methods.…”

Section: Introductionmentioning

confidence: 99%

Palladium‐catalyzed reductive homocoupling of aryl sulfonates via cleavage of C─O bond at room temperature

Zhong

Chen²,

Liu³

et al. 2017

Applied Organom Chemis

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Palladium‐catalyzed reductive homocoupling of aryl sulfonates has been successfully achieved under mild conditions. This transformation is a new method for the homocoupling reaction of aryl sulfonates at room temperature via the cleavage of C─O bonds, thus providing an alternative synthesis of symmetric biaryls. The reported reductive homocoupling reaction is tolerant of many common functional groups regardless of electron‐donating or electron‐withdrawing nature, making this newly developed transformation important for complementing Ullmann coupling. Experimental Section. Typical procedure for the products.

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Homocoupling of arylboronic acids catalyzed by simple gold salts

Cited by 33 publications

References 54 publications

Homocoupling of Phenylboronic Acid using Atomically Dispersed Gold on Carbon Catalysts: Catalyst Evolution Before Reaction

Homocoupling of Phenylboronic Acid using Atomically Dispersed Gold on Carbon Catalysts: Catalyst Evolution Before Reaction

The Homocoupling of Arylsulfonylhydrazides by Palladium-Catalysed Desulfonation in Air

Palladium‐catalyzed reductive homocoupling of aryl sulfonates via cleavage of C─O bond at room temperature

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