24085-65-2

Upstream product

• 98-54-4 para-tert-butylphenol 
• 3972-65-4 1-bromo-4-tert-butylbenzene 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 253185-03-4 tert-butylbenzene 
• 50-00-0 formaldehyd 
• 31166-44-6 phenylmethyl 1-piperazinecarboxylate 
• 35779-04-5 1-tert-butyl-4-iodobenzene 

Downstream Products

• 253185-03-4 tert-butylbenzene 
• 98-54-4 para-tert-butylphenol 
• 90-47-1 xanth-9-one 
• 92-83-1 xanthene 

Relevant academic research and scientific papers

Catalytic conversion of 4-tert-butylphenol in hydrogen peroxide solutions in the presence of titanium oxide compounds and titanosilicates

The catalytic conversion of 4-tert-butylphenol (TBP) in hydrogen peroxide solutions in the presence of titanium oxide samples with different phase compositions and crystalline and amorphous titanosilicate samples has been studied. It has been shown that microporous crystalline titanosilicate TS-1 exhibits low activity in the TBP conversion owing to steric restrictions to the diffusion of the substrate molecules to catalytically active sites. The samples of titanium oxide compounds and mesoporous titanosilicates exhibit similar activity, while the selectivity of the latter for 4-tert-butylcatechol (TBC) is higher. The effect of the mesoporous titanosilicate concentration in the reaction mixture and the test temperature and duration on the TBP conversion and the TBC selectivity has been determined.

Visible-Light Photoredox Catalyzed Dehydrogenative Synthesis of Allylic Carboxylates from Styrenes

The visible-light photoredox/[Co(III)] cocatalyzed dehydrogenative functionalization of cyclic and acyclic styryl derivatives with carboxylic acids is documented. The methodology enables the chemo- and regioselective allylic functionalization of styryl compounds, leading to allylic carboxylates (32 examples) under stoichiometric acceptorless conditions. Intermolecular as well as intramolecular variants are documented in high yields (up to 82%). A mechanistic rationale is also proposed on the basis of a combined experimental and spectroscopic investigation.

Synthesis and Characterization of Acridinium Dyes for Photoredox Catalysis

Photoredox catalysis is a rapidly evolving platform for synthetic methods development. The prominent use of acridinium salts as a sustainable option for photoredox catalysts has driven the development of more robust and synthetically useful versions based on this scaffold. However, more complicated syntheses, increased cost, and limited commercial availability have hindered the adoption of these catalysts by the greater synthetic community. By utilizing the direct conversion of a xanthylium salt into the corresponding acridinium as the key transformation, we present an efficient and scalable preparation of the most synthetically useful acridinium reported to date. This divergent strategy also enabled the preparation of a suite of novel acridinium dyes, allowing for a systematic investigation of substitution effects on their photophysical properties.

Cu-Catalyzed Couplings of Heteroaryl Primary Amines and (Hetero)aryl Bromides with 6-Hydroxypicolinamide Ligands

A family of 6-hydroxypicolinamide ligands have been identified as effective supporting ligands for Cu-catalyzed couplings of heteroaryl bromides and chlorides with heteroaryl primary amines. The C-N couplings are carried out at 80-120 °C in DMSO or sulfolane using K2CO3 or K3PO4 as the base with 2-10 mol % CuI and supporting ligand. The strength of the base was found to have an impact on the chemoselectivity and rate. The use of K2CO3 as the base enabled selective C-N coupling of aryl bromides over aryl chlorides with 2-5 mol % Cu at 80-120 °C. With K3PO4 as the base, aryl chlorides are capable of undergoing C-N coupling, though 5-10 mol % Cu is required at 120-130 °C. Members of the ligand family are straightforward to prepare in one step from 6-hydroxypicolinic acid and the corresponding anilines.

Reductive Cleavage of C—O Bond in Model Compounds of Lignin

A simple protocol for reductive cleavage of C—O bond in diaryl and aryl methyl ethers was reported, in which NaH served as a reducing agent and KOtBu as a base and a radical initiator. The combination of NaH and KOtBu displayed high efficiency for reductive cleavage of C—O bond in diaryl and aryl ethers (e.g., dibenzofuran, diphenyl ether, anisole) without the hydrogenation of the aryl rings, in the absence of any other catalysts or ligands at 140 °C, producing corresponding arenes and phenols. It was indicated that the reaction was under a radical mechanism.

Reductive cleavage of inert aryl C-O bonds to produce arenes

Reductive cleavage of the aryl C-O bonds in various phenolic compounds and aryl ethers was achieved using LiAlH4 combined with KOtBu and without any other catalysts or additives, solely producing arenes in high yields.

Palladium-catalyzed C-O bond formation: direct synthesis of phenols and aryl/alkyl ethers from activated aryl halides

A simple and efficient palladium-catalyzed carbon-oxygen bond formation is reported. The palladium-tri-tert-butylphosphine complex was found to be effective in converting haloarenes to corresponding substituted phenols. This methodology offers a direct transformation of aryl halides to phenols, as well as the straightforward application to generate a wide variety of diaryl or alkyl/aryl ethers.

Process for arylating or vinylating or alkynating a nucleophilic compound

The present invention concerns a process for arylating or vinylating or alkynating a nucleophilic compound. More particularly, the invention concerns arylating nitrogent-containing organic derivatives. The arylating or vinylating or alkynating process of the invention consists of reacting a nucleophilic compound with a compound carrying a leaving group and is characterized in that the reaction is carried out in the presence of an effective quantity of a catalyst based on a metallic element M selected from groups (VIII), (Ib) and (IIb) of the periodic table and at least one at least bidentate ligand comprising at least two chelating atoms, namely at least one oxygen atom and at least one nitrogen atom.

Synthesis of symmetrical diaryl ethers from arylboronic acids mediated by copper(II) acetate

Copper promoted generation of phenols in situ through arylation of water and their subsequent arylation with arylboronic acids affords a wide range of symmetrical diaryl ethers in good to high yield. The reaction is rapid, mild, convenient and tolerant of a wide range of functionalities on the arylboronic acid.