PdCl<sub>2</sub> and <i>N</i>‐Hydroxyphthalimide Co‐catalyzed CH Hydroxylation by Dioxygen Activation

Yan, Yuepeng; Peng, Feng; Zheng, Qing‐Zhong; Liang, Yu‐Feng; Lu, Jingfen; Cui, Yuxin; Jiao, Ning

doi:10.1002/anie.201300957

Cited by 208 publications

(87 citation statements)

References 97 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In 2013, Jiao and coworkers described the use of N -hydroxyphthalimide to mediate autoxidation of toluene to generate a reactive oxidant in chelate-directed Pd-catalyzed arene hydroxylation. 19 Although certain details of their proposed mechanism differ from Scheme 5, both reactions exploit autoxidation of a weak C–H bond in the solvent to generate an O 2 -derived peroxide capable of oxidizing an arylpalladium(II) intermediate to a higher oxidation state, resulting in facile carbon-heteroatom bond formation. Overall, this concept represents an unusual, but valuable strategy to use O 2 as a stoichiometric oxidant in Pd-catalyzed oxidation reactions.…”

Section: Discussionmentioning

confidence: 99%

Palladium catalyzed aryl C–H amination with O₂via in situ formation of peroxide-based oxidant(s) from dioxane

Weinstein

Stahl

2014

Catal. Sci. Technol.

View full text Add to dashboard Cite

(DAF)Pd(OAc)2 (DAF = 4,5-diazafluorenone) catalyzes aerobic intramolecular aryl C–H amination with N-benzenesulfonyl-2-aminobiphenyl in dioxane to afford the corresponding carbazole product. Mechanistic studies show that the reaction involves in situ generation of peroxide species from 1,4-dioxane and O2, and the reaction further benefits from the presence of glycolic acid, an oxidative decomposition product of dioxane. An induction period observed for the formation of the carbazole product correlates with the formation of 1,4-dioxan-2-hydroperoxide via autoxidation of 1,4-dioxane, and the in situ-generated peroxide is proposed to serve as the reactive oxidant in the reaction. These findings have important implications for the palladium-catalyzed aerobic oxidation reactions conducted in ethereal solvents.

show abstract

Section: Discussionmentioning

confidence: 99%

Palladium catalyzed aryl C–H amination with O₂via in situ formation of peroxide-based oxidant(s) from dioxane

Weinstein

Stahl

2014

Catal. Sci. Technol.

View full text Add to dashboard Cite

show abstract

“…3,4 Phenol is an instance of such type of compound, which is the major source of bakelite and phenol resins, which are utilized in many industries over the world. 5 The industrial demand for phenol is increasing every year and its production currently it has been exceeded 7.2 megaton per year.…”

mentioning

confidence: 99%

Synergistic Effect between Ultrasmall Cu(II) Oxide and CuCr₂O₄ Spinel Nanoparticles in Selective Hydroxylation of Benzene to Phenol with Air as Oxidant

et al. 2015

View full text Add to dashboard Cite

Phenol is an important commodity chemical and the catalytic conversion of benzene to phenol by molecular oxygen with minimum waste production is of high significance from an academic as well as industrial point of view. We have developed a facile synthesis method for the preparation of 2-8 nm Cu (II) oxide nanoparticles supported on CuCr 2 O 4 spinel nanoparticles (with size ~55 nm).Detailed characterization of the material was carried out by XRD, SEM, TEM, XPS, FTIR, TGA, TPR, BET surface area, XANES and ICP-AES. XRD and XPS analyses revealed that the main phase is CuCr 2 O 4 spinel, where small amount of CuO is dispersed on it. The catalyst was highly active for selective oxidation of benzene to phenol with air as oxidant. The influence of reaction parameters was investigated in detail. The high catalytic performance of the catalyst is due to ultrasmall size of Cu (II) oxide nanoparticle and the strong synergy between ultrasmall Cu(II) oxide and CuCr 2 O 4 spinel nanoparticles that plays pivotal role in activating air to generate active oxygen species which accomplishes benzene to phenol conversion (36%) with very high selectivity (78%) in a continuous process.

show abstract

“…In 2013, Jiao and co-workers reported a hydroxylation protocol for (2-pyridyl)arenes using PdCl 2 and N -hydroxyphthalimide (NHPI) as catalyst and molecular oxygen as oxidant [60]. (2-Pyridyl)arenes were converted to the hydroxylated products in toluene at 100 °C (Scheme 31).…”

Section: Reviewmentioning

confidence: 99%

Transition-metal-catalyzed synthesis of phenols and aryl thiols

Liu¹,

Li²,

Yan³

2017

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Phenols and aryl thiols are fundamental building blocks in organic synthesis and final products with interesting biological activities. Over the past decades, substantial progress has been made in transition-metal-catalyzed coupling reactions, which resulted in the emergence of new methods for the synthesis of phenols and aryl thiols. Aryl halides have been extensively studied as substrates for the synthesis of phenols and aryl thiols. In very recent years, C–H activation represents a powerful strategy for the construction of functionalized phenols directly from various arenes. However, the synthesis of aryl thiols through C–H activation has not been reported. In this review, a brief overview is given of the recent advances in synthetic strategies for both phenols and aryl thiols.

show abstract

PdCl₂ and N‐Hydroxyphthalimide Co‐catalyzed CH Hydroxylation by Dioxygen Activation

Abstract: Scheme 1. Hydroxylation of C sp 2ÀH bonds. BQ = benzoquinone, DG = directing group.

Cited by 208 publications

References 97 publications

Palladium catalyzed aryl C–H amination with O₂via in situ formation of peroxide-based oxidant(s) from dioxane

Palladium catalyzed aryl C–H amination with O₂via in situ formation of peroxide-based oxidant(s) from dioxane

Synergistic Effect between Ultrasmall Cu(II) Oxide and CuCr₂O₄ Spinel Nanoparticles in Selective Hydroxylation of Benzene to Phenol with Air as Oxidant

Transition-metal-catalyzed synthesis of phenols and aryl thiols

Contact Info

Product

Resources

About

PdCl2 and N‐Hydroxyphthalimide Co‐catalyzed CH Hydroxylation by Dioxygen Activation

Abstract: Scheme 1. Hydroxylation of C sp 2ÀH bonds. BQ = benzoquinone, DG = directing group.

Cited by 208 publications

References 97 publications

Palladium catalyzed aryl C–H amination with O2via in situ formation of peroxide-based oxidant(s) from dioxane

Palladium catalyzed aryl C–H amination with O2via in situ formation of peroxide-based oxidant(s) from dioxane

Synergistic Effect between Ultrasmall Cu(II) Oxide and CuCr2O4 Spinel Nanoparticles in Selective Hydroxylation of Benzene to Phenol with Air as Oxidant

Transition-metal-catalyzed synthesis of phenols and aryl thiols

Contact Info

Product

Resources

About

PdCl₂ and N‐Hydroxyphthalimide Co‐catalyzed CH Hydroxylation by Dioxygen Activation

Palladium catalyzed aryl C–H amination with O₂via in situ formation of peroxide-based oxidant(s) from dioxane

Palladium catalyzed aryl C–H amination with O₂via in situ formation of peroxide-based oxidant(s) from dioxane

Synergistic Effect between Ultrasmall Cu(II) Oxide and CuCr₂O₄ Spinel Nanoparticles in Selective Hydroxylation of Benzene to Phenol with Air as Oxidant