Palladium-imidazolinium carbene-catalyzed arylation of aldehydes with arylboronic acids in water

Kuriyama, Masami; Ishiyama, Natsuki; Shimazawa, Rumiko; Onomura, Osamu

doi:10.1016/j.tet.2010.06.049

Cited by 22 publications

(11 citation statements)

References 79 publications

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“…Based on the positive results obtained for the benzhydrols, the newly developed methodology was applied to the more challenging carbohydrate substrates. It should be noted that many of the previous methodologies for the preparation of glycosyl azides rely on Mitsunobu‐like conditions with metal azides and hydrazoic acid or by the reaction of unstable glycosyl halides with sodium azide . Remarkably, the conditions used for the benzhydrols led to a 67 % yield with an α/β ratio of 3.3:1 when applied to 2,3,5‐tri‐O‐benzyl‐ β ‐D‐arabinofuranose.…”

Section: Resultsmentioning

confidence: 99%

“…(4‐Formylphenyl)(phenyl)methanol (S6): The title compound was prepared from 4‐(diethoxylmethyl) benzaldehyde (300 mg, 1.44 mmol, 1.0 eq.) and phenylmagnesium bromide (391 mg, 2.16 mmol, 1.5 eq.)…”

Section: Methodsmentioning

confidence: 99%

“…in dry THF (6 mL) following general procedure 2.1. Isolation of the product was achieved by flash column chromatography using hexanes/ethyl acetate (9:1) to afford the product as a pale yellow oil (207 mg, 64 % (4-Formylphenyl)(phenyl)methanol (S6): [27] The title compound was prepared from 4-(diethoxylmethyl) benzaldehyde (300 mg, 1.44 mmol, 1.0 eq.) and phenylmagnesium bromide (391 mg, 2.16 mmol, 1.5 eq.)…”

Section: General Procedures For the Preparation Of Benzhydryl Alcoholsmentioning

confidence: 99%

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A Direct Brønsted Acid‐Catalyzed Azidation of Benzhydrols and Carbohydrates

2019

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Benzhydryl alcohols were converted into their corresponding diarylazidomethane analogues using azidotrimethylsilane (TMSN3) in the presence of a catalytic amount of a Brønsted acid HBF4·OEt2. The azidation reactions proceeded in high yields and demonstrated excellent functional group tolerance to electron‐donating and electron‐withdrawing substituents. In addition, a range of unprotected functional groups including amine, amide, aldehyde and alcohol were well‐tolerated. Furthermore, this methodology was successfully applied to carbohydrates for the preparation of the corresponding azide derivatives.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: General Procedures For the Preparation Of Benzhydryl Alcoholsmentioning

confidence: 99%

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A Direct Brønsted Acid‐Catalyzed Azidation of Benzhydrols and Carbohydrates

2019

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“…In addition to the above-mentioned additions of diverse boronic acids to activated and non-activated double bonds, more traditional 1,2-addition reactions with C-heteroatom double bonds have been described. Thus, the organocatalytic formylation of boronic acids with glyoxylic acid [199], the palladium-imidazolinium carbene-catalyzed arylation of aldehydes with boronic acids [200], the rhodium-catalyzed addition of boronic acids to 2,2-disubstituted malononitriles [201,202], the rhodium-catalyzed addition of boronic acids to α-ketoesters [203], and the addition of boronic acids to nitrosoarenes [204] are all valuable examples.…”

Section: Chemical Transformations Of Indolylboronic Acid Derivativesmentioning

confidence: 99%

Indolylboronic Acids: Preparation and Applications

et al. 2019

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Indole derivatives are associated with a variety of both biological activities and applications in the field of material chemistry. A number of different strategies for synthesizing substituted indoles by means of the reactions of indolylboronic acids with electrophilic compounds are considered the methods of choice for modifying indoles because indolylboronic acids are easily available, stable, non-toxic and new reactions using indolylboronic acids have been described in the literature. Thus, the aim of this review is to summarize the methods available for the preparation of indolylboronic acids as well as their chemical transformations. The review covers the period 2010–2019.

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“…Then, only thioether-imidazolinium chloride 6e was proven to be an effective N-heterocyclic carbene ligand precursor (entries 1-6). 45) Evaluation on the effect of organic solvents revealed that smooth reaction progress required appropriate solvent polarity (entries 7-9). Interestingly, dimethyl sulfoxide (DMSO) gave a quite poor result although the reaction in more highly polar water proceeded efficiently, which could be achieved by hydrophobic effects.…”

Section: Palladium-catalyzed 12-addition Of Organoboronic Acids To Amentioning

confidence: 99%

Development of Efficient Catalytic Arylation of Aldehydes with Thioether-Imidazolinium Carbene Ligands

Kuriyama

2012

CHEMICAL & PHARMACEUTICAL BULLETIN

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Effective methods of ligand design have been highly sought due to the significant roles of ligands in controlling metal catalyses. In particular, easy-to-handle ligands to realize high reaction efficacy, substrate tolerance, and environmental friendliness are desirable. Novel bidentate ligands containing N-heterocyclic carbene and thioether moieties were developed based on findings of hemilabile coordination, whose precursors were crystalline solids stable enough to handle and store in the air. The thioether-imidazolinium carbene ligand successfully brought out high catalyst performance of palladium in the catalytic arylation of aldehydes with organoboron reagents, which tolerated a diverse range of substrates including poorly reactive, sterically hindered, and heterocyclic compounds. This process was applied to gram-scale synthesis using only water as solvent with high efficiency and also achieved the effective one-pot synthesis of 3-arylphthalides known as useful biologically active agents and important synthetic intermediates for naturally occurring compounds.

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Palladium-imidazolinium carbene-catalyzed arylation of aldehydes with arylboronic acids in water

Cited by 22 publications

References 79 publications

A Direct Brønsted Acid‐Catalyzed Azidation of Benzhydrols and Carbohydrates

A Direct Brønsted Acid‐Catalyzed Azidation of Benzhydrols and Carbohydrates

Indolylboronic Acids: Preparation and Applications

Development of Efficient Catalytic Arylation of Aldehydes with Thioether-Imidazolinium Carbene Ligands

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