3169-72-0

Upstream product

• 98-54-4 para-tert-butylphenol 
• 88-73-3 2-Chloronitrobenzene 
• 59970-38-6 4-tert-butylphenyl mesylate 
• 1493-27-2 ortho-nitrofluorobenzene 
• 577-19-5 2-nitrophenyl bromide 

Downstream Products

• 1527494-35-4 1-(4-(tert-butyl)phenoxy)-2-iodobenzene 
• 3169-73-1 4-tert-butyl-1-(2-aminophenoxy)benzene 

Relevant academic research and scientific papers

Distance-Dependent Attractive and Repulsive Interactions of Bulky Alkyl Groups

The stabilizing and destabilizing effects of alkyl groups on an aromatic stacking interaction were experimentally measured in solution. The size (Me, Et, iPr, and tBu) and position (meta and para) of the alkyl groups were varied in a molecular balance mod

Four- and Sixfold Tandem-Domino Reactions Leading to Dimeric Tetrasubstituted Alkenes Suitable as Molecular Switches

A highly efficient palladium-catalyzed fourfold tandem-domino reaction consisting of two carbopalladation and two C-H-activation steps was developed for the synthesis of two types of tetrasubstituted alkenes 3 and 6 with intrinsic helical chirality starting from substrates 1 and 4, respectively. A sixfold tandem-domino reaction was also developed by including a Sonogashira reaction. 20 compounds with different substitution patterns were prepared with yields of up to 97%. Structure elucidation by X-ray crystallography confirmed helical chirality of the two alkene moieties. Photophysical investigations of some of the compounds showed pronounced switching properties through light-controlled changes of their stereochemical configuration.

Chemoselective arylation of phenols with bromo-nitroarenes: Synthesis of nitro-biaryl-ols and their conversion into benzofurans and carbazoles

A series of electron withdrawing or donating group substituted phenols were chemoselectively arylated with various substituted bromo-nitroarenes using KOtBu at room temperature via an SNAr pathway. The synthesis of natural alkaloids (carbazoles), dibenzofurans, and a biaryl-indole was achieved from the synthesized nitro-biaryl-ols. This journal is the Partner Organisations 2014.

A Fast Way to Fluorescence: A Fourfold Domino Reaction to Condensed Polycyclic Compounds

A fast and efficient palladium-catalyzed fourfold domino Sonogashira/double-carbopalladation/C H-activation reaction that converts simple aromatic systems into complex polycyclic hydrocarbons has been developed. A number of substituted products has thus been prepared in yields up to 89 %. The structural assignment has been confirmed by using single-crystal X-ray crystallography. The products show intriguing fluorescence activity and thus might serve as chemical sensors or fluorescent imaging dyes.

Palladium supported on zinc ferrite: An efficient catalyst for ligand free C-C and C-O cross coupling reactions

An efficient superparamagnetic Pd-ZnFe2O4 solid catalyst has been synthesized by loading Pd(0) species on zinc ferrite nanoparticles. Sonogashira cross couplings between terminal alkynes and aryl halides were achieved in the absence of any Cu co-catalyst. A Heck-Matsuda coupling reaction of structurally different aryldiazonium tetrafluoroborate substrates was preceded at 40 C in water. Cyanation of aryl halides was successfully done using K4[Fe(CN)6] as the cyanide source over Pd-ZnFe2O4. The catalyst was also employed for Ullmann type cross coupling reactions. Excellent yield of the products, reusability, and uncomplicated work-up make this catalyst efficient for C-C and C-O coupling reactions. Good yield of products, easy separation, and negligible leaching of Pd from the catalyst surface confirm the true heterogeneity in these catalytic reactions.

Potassium fluoride supported on natural nanoporous zeolite: A new solid base for the synthesis of diaryl ethers

An efficient and inexpensive synthesis of diaryl ethers has been developed. The process involves the nucleophilic aromatic substitution of electron-deficient aryl halides and phenols and is mediated by potassium fluoride/Clinoptilolite (KF/CP) in dimethyl sulfoxide (DMSO). The approach affords good to excellent yields of the arylated products without the need for additional cation capture. The solid base is also efficient in the Ullmann ether synthesis. A new, inexpensive solid base for the synthesis of diaryl ethers has been developed. Clinoptilolite, a natural zeolite with a high tendency for cation capture, combined with potassium fluoride, provides an efficientsolid base for the deprotonation of phenols in nucleophilic reactions. The same solid base acts as a reliable base for the copper-catalyzed synthesis of diaryl ethers. Copyright

Microwave-assisted construction of diaryl ethers directly from arylmethanesulfonates as convenient latent phenols with aryl halides

The microwave-assisted synthesis of diaryl ethers directly from aryl halides and arylmethanesulfonates, which as latent phenols obviate a deprotection step prior to the SNAr reaction, in the presence of Cs2CO3 is described. The reaction time was very short (6-9-min), and good to excellent yields (53-90%) with the wide substrate scope were achieved without any catalyst. Copyright Taylor & Francis Group, LLC.

C(aryl)-O bond formation from aryl methanesulfonates via consecutive deprotection and SNAr reactions with aryl halides in an ionic liquid

An efficient K3PO4-mediated synthesis of unsymmetrical diaryl ethers using the ionic liquid [Bmim]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) as solvent has been developed. The procedure involves consecutive deprotection of aryl methanesulfonates and a nucleophilic aromatic substitution (SNAr) with activated aryl halides.