The First General and Selective Palladium(II)‐Catalyzed Alkoxycarbonylation of Arylboronates: Interplay among Benzoquinone‐Ligated Palladium(0) Complex, Organoboron, and Alcohol Solvent

Yamamoto, Yoshihiko

doi:10.1002/adsc.200900836

Cited by 60 publications

(38 citation statements)

References 114 publications

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“…Then, concentration was performed under reduced pressure. The crude product obtained was purified by column chromatography (petroleum ether/ ethyl acetate (PE/EA) = 12:1) on silica gel to provide the desired compound Methyl 2-acetylbenzoate (1a): [15] 202.5, 166.6, 142.3, 131.6, 129.6, 129.3, 128.7, 126.1, 61.2, 30.0, 13.6 ppm.…”

Section: Experimental Section Generalp Roceduresmentioning

confidence: 99%

Ruthenium‐Catalyzed Enantioselective Hydrogenation/Lactonization of 2‐Acylarylcarboxylates: Direct Access to Chiral 3‐Substituted Phthalides

et al. 2017

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Highly enantioselective tandem hydrogenation/lactonization of various 2‐acylarylcarboxylates including 2‐aroylarylcarboxylates were realized by using [RuCl(benzene)(S)‐SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3‐substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram‐scale reaction was performed to further demonstrate the practicality of this approach.

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Section: Experimental Section Generalp Roceduresmentioning

confidence: 99%

Ruthenium‐Catalyzed Enantioselective Hydrogenation/Lactonization of 2‐Acylarylcarboxylates: Direct Access to Chiral 3‐Substituted Phthalides

et al. 2017

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“…An original oxidative transmetalation mechanism, supported by theoretical calculations based on the DFT and MP2 methods, was proposed for the palladium‐catalyzed alkoxycarbonylation of arylboronates 14. The catalytic cycle starts from the Pd 0 complex 10A (Scheme ).…”

Section: Bq As Promoter Of Transmetalationmentioning

confidence: 99%

“…Yamamoto observed that the BQ‐ligated palladium(0) complex Pd(BQ)(cod) (cod = cycloocta‐1,5‐diene) was almost unreactive towards p ‐tolylboronic acid in CDCl 3 , whereas the addition of CD 3 OD led to the formation of the homocoupling product in good yields, together with hydroquinone (Scheme ) 14. This results suggests that methanol acts as a proton donor for the oxidation of Pd 0 in this particular system, hence the transmetalation of the boronic acid leading to the coupling reaction.…”

Section: 1 Regeneration Of Active Pdii Species From Pd0mentioning

confidence: 99%

Ubiquitous Benzoquinones, Multitalented Compounds for Palladium‐Catalyzed Oxidative Reactions

Vasseur¹,

Мuzart²,

Bras³

2015

Eur J Org Chem

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Palladium(II)‐catalyzed procedures often use benzoquinone (BQ) to regenerate the catalyst. Besides its oxidation role, BQ can also promote various steps of the catalytic cycle. This review highlights the multifaceted properties of BQ and its analogues when involved in PdII‐catalyzed oxidative reactions and presents mechanisms proposed in the literature, in some cases with personal observations.

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“…Conversely, Yamamoto et al. described a general and selective palladium‐catalyzed oxidative carbonylation of arylboronates in alcohols 49. In the presence of Pd(OAc) 2 /PPh 3 and BQ, esters were produced from the corresponding arylboronates in good yields at room temperature (Scheme ).…”

Section: Oxidative Carbonylation Of Organometallic Reagentsmentioning

confidence: 99%

Palladium‐Catalyzed Oxidative Carbonylation Reactions

Wu¹,

Neumann²,

Beller³

2013

ChemSusChem

308

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Palladium-catalyzed coupling reactions have become a powerful tool for advanced organic synthesis. This type of reaction is of significant value for the preparation of pharmaceuticals, agrochemicals, as well as advanced materials. Both, academic as well as industrial laboratories continuously investigate new applications of the different methodologies. Clearly, this area constitutes one of the major topics in homogeneous catalysis and organic synthesis. Among the different palladium-catalyzed coupling reactions, several carbonylations have been developed and widely used in organic syntheses and are even applied in the pharmaceutical industry on ton-scale. Furthermore, methodologies such as the carbonylative Suzuki and Sonogashira reactions allow for the preparation of interesting building blocks, which can be easily refined further on. Although carbonylative coupling reactions of aryl halides have been well established, palladium-catalyzed oxidative carbonylation reactions are also interesting. Compared with the reactions of aryl halides, oxidative carbonylation reactions offer an interesting pathway. The oxidative addition step could be potentially avoided in oxidative reactions, but only few reviews exist in this area. In this Minireview, we summarize the recent development in the oxidative carbonylation reactions.

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The First General and Selective Palladium(II)‐Catalyzed Alkoxycarbonylation of Arylboronates: Interplay among Benzoquinone‐Ligated Palladium(0) Complex, Organoboron, and Alcohol Solvent

Abstract: Methoxycarbonylation of aryl-and alken-

Cited by 60 publications

References 114 publications

Ruthenium‐Catalyzed Enantioselective Hydrogenation/Lactonization of 2‐Acylarylcarboxylates: Direct Access to Chiral 3‐Substituted Phthalides

Ruthenium‐Catalyzed Enantioselective Hydrogenation/Lactonization of 2‐Acylarylcarboxylates: Direct Access to Chiral 3‐Substituted Phthalides

Ubiquitous Benzoquinones, Multitalented Compounds for Palladium‐Catalyzed Oxidative Reactions

Palladium‐Catalyzed Oxidative Carbonylation Reactions

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