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Upstream product

• 732-26-3 2,4,6-tri-tert-butylphenoxol 
• 107-12-0 propiononitrile 
• 107-10-8 propylamine 
• 1020-31-1 3,5-Di-tert-butylcatechol 
• 96-76-4 2,4-di-tert-Butylphenol 

Relevant academic research and scientific papers

Selective Aerobic C-H Amination of Phenols with Primary Amines over Copper toward Benzoxazoles

Using O2 as the oxidant, the benzoxazole frameworks can be directly constructed from the readily available phenols and primary amines in the presence of NH4PF6 over copper under mild conditions. Mechanistic studies showed

Consecutive Oxidation/Condensation/Cyclization/Aromatization Sequences Catalyzed by Nanostructured Iron(III)-Porphyrin Complex towards Benzoxazole Derivatives

A facile, efficient, and eco-friendly strategy to access benzoxazole heterocyclic products has been accomplished through oxidation of catechols followed by condensation/cyclization/aromatization sequences. This process is catalyzed by nanostructured iron(III)-porphyrin complex to form desired benzoxazole derivatives at room temperature under air condition. The procedure is widely applicable to diverse amines, and can provide the heterocyclic products in a scalable fashion, as well. One of the most significant types of oxidizing agents in nature is the iron-porphyrin complexes (0.1 mol-%), existing in the structure of hemoglobin. They have benefits such as low toxicity and high oxidation potential for many substrates.

Amino Acids: Nontoxic and Cheap Alternatives for Amines for the Synthesis of Benzoxazoles through the Oxidative Functionalization of Catechols

The nano magnetic Fe3O4 (NM?Fe3O4) was applied for the synthesis of benzoxazoles via a C(aryl)?OH functionalization of catechol derivatives and amines in ethanol at room temperature. In the next step, amino acids have been applied as nontoxic and cheap alternatives for amines. The obtained products were similar with the regular amines case. This is the first report about the application of amino acids as alternatives for primary amines in organic synthesis. Furthermore, the presented method was successfully applied toward the synthesis of desired products in large scales. (Figure presented.).

METHOD FOR PRODUCING AN ARENE WITH AN AROMATIC C-N BOND ORTHO TO AN AROMATIC C-O BOND

A method for producing an arene with an aromatic C—N bond ortho to an aromatic C—O bond from a hydroxy arene comprising said aromatic C—O bond is provided. This method comprising the steps a) ortho-oxygenating the hydroxy arene to produce an ortho-quinone, b) condensating the ortho-quinone with a nitrogen nucleophile to generate a compound of Formula (IVa) or (IVb), and c) allowing 1,5-hydrogen atom shift of the compound of Formula (IVa) or (IVb), thereby producing arenes with a C—N bond ortho to a C—O bond of Formula (Va) and (Vb), respectively:

OMS-2-Supported Cu Hydroxide-Catalyzed Benzoxazoles Synthesis from Catechols and Amines via Domino Oxidation Process at Room Temperature

In the presence of manganese oxide octahedral molecular sieve (OMS-2) supported copper hydroxide Cu(OH)x/OMS-2, aerobic synthesis of benzoxazoles from catechols and amines via domino oxidation/cyclization at room temperature is achieved. This heterogeneous benzoxazoles synthesis initiated by the efficient oxidation of catechols over Cu(OH)x/OMS-2 tolerates a variety of substrates, especially amines containing sensitive groups (hydroxyl, cyano, amino, vinyl, ethynyl, ester, and even acetyl groups) and heterocycles, which affords functionalized benzoxazoles in good to excellent yields by employing low catalyst loading (2 mol % Cu). The characterization and plausible catalytic mechanism of Cu(OH)x/OMS-2 are described. The notable features of our catalytic protocol such as the use of air as the benign oxidant and EtOH as the solvent, mild conditions, ease of product separation, being scalable up to the gram level, and superior reusability of catalyst (up to 10 cycles) make it more practical and environmentally friendly for organic synthesis.

Copper-Catalyzed Aerobic Oxidative C(aryl)-OH Bond Functionalization of Catechols with Amines Affording Benzoxazoles

The first copper-catalyzed aerobic oxidative C(aryl)-OH bond functionalization of catechols is reported. Under air, at room temperature, in the presence of a copper catalyst, catechols react with amines to produce the corresponding benzoxazoles in high yields. Mechanistic studies suggest that the reaction proceeds via an intriguing competitive oxidation and a synergetic catalysis between catechol and amine.

Reactions of Phenols with Thianthrene Cation Radical

The phenols 2-R1-6-R2-phenol 1a-g in which R1 = R2 = tert-butyl, methyl, isopropyl, Cl, Br, F, and H reacted with thianthrene cation radical perchlorate (TH+ClO4-) to give 5-(4-hydroxyaryl)thianthreniumyl perchlorates 2a-g in good yield. o-Allylphenol (1i) behaved similarly. o-tert-Butylphenol (1h) gave both 5-(3-tert-butyl-4-hydroxyphenyl)thianthreniumyl perchlorate (2h) and a quinonoidal perchlorate (3), namely, 5-(3-thianthreniumyl-5-tert-butyl-6-oxo-2,4-cyclohexadien-1-ylidene)-5,5-dihydrothianthrene perchlorate.The 2,6-di-tert-butyl-4-R3-phenols 4a-c, R3 = tert-butyl, methoxy, and methyl, reacted with Th+ClO4- in nitrile solvents (RCN) to give 2-R-5-R3-7-tert-butylbenzoxazoles 5a-e.The tert-butyl group that was displaced by RCN in forming 5 was converted into t-BuNHCOR (8), tert-butyl alcohol, and isobutene.In contrast, 2-tert-butyl-4,6-dimethylphenol (9) gave, in CH3CN, 4-tert-butyl-2,5,7-trimethylbenzoxazole (11), that is, with migration of the displaced tert-butyl group.The reactions of 4-tert-butylphenol (14) and 2,4-di-tert-butylphenol (17) are also described.