4475-59-6

Upstream product

• 371-41-5 4-Fluorophenol 
• 1493-27-2 ortho-nitrofluorobenzene 
• 1765-93-1 4-fluoroboronic acid 
• 372-20-3 3-fluorophenol 
• 23530-43-0 2-(N,N-dimethylaminosulfonyl)nitrobenzene 

Downstream Products

• 3169-71-9 1-(4-fluorophenoxy)-2-aminobenzene 
• 1316273-86-5 N-[2-(4-fluorophenoxy)phenyl]acetamide 
• 203303-06-4 1-(4-fluorophenoxy)-2-iodobenzene 
• 640766-67-2 2-(3-fluorophenoxy)aniline 

Relevant academic research and scientific papers

Ligand-free copper-catalyzed O-arylation of arenesulfonamides with phenols: An unusual approach to biaryl ether synthesis

An unprecedented ligand-free copper-catalyzed O-arylation of arenesulfonamides with phenols has been developed. Thus, a range of unsysmmetric biaryl ethers were synthesized in excellent yields. The reaction occurs efficiently with excellent regioselectivity through the cleavage of Cary–S bond and with a good tolerance of functional groups on the phenyl ring of phenols. The reaction is appreciated for its readily accessible substrates, mild conditions, and simple operation under air.

Diphenyl ether derivatives occupy the expanded binding site of cyclohexanedione compounds at the colchicine site in tubulin by movement of the αT5 loop

Microtubule targeting agents represent a very active arena in the development of anticancer agents. In particular, compounds binding at the colchicine site in tubulin are being deeply studied, and the structural information recently available on this binding site allows structure-directed design of new ligands. Structural comparison of our recently reported high resolution X-Ray structure of the cyclohexanedione derivative TUB075 bound to tubulin and the tubulin-DAMA-colchicine complex has revealed a conformational change in the αT5 loop. By a grid-based computational analysis of the tubulin-DAMA-colchicine binding site, we have identified a new favourable binding area in the colchicine-site that was unexplored by our lead TUB075. Thus, based on a structure-guided design, new cyclohexanedione derivatives have been synthesized and tested for tubulin binding and in cellular assays. As a result, we have identified diphenyl ether derivatives with IC50 values around 10–40 nM against three different tumor cell lines and affinity constants for tubulin similar to that of colchicine around 107 M?1. As expected, they halted the cell cycle progression at G2/M phase at concentrations as low as 0.08 μM.

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.

Synthesis of unsymmetrical biaryl ethers through nickel-promoted coupling of polyfluoroarenes with arylboronic acids and oxygen

Polyfluoro-substituted unsymmetrical biaryl ethers were synthesized via a novel Ni-catalyzed cross-coupling reaction of polyfluoroarenes with arylboronic acids and oxygen. The polyfluorinated arenes presumably captured the phenoxide intermediate efficiently, which made the oxygen-insertion proceed smoothly via the SNAr protocol. The 18O labeling experiment demonstrated that the oxygen introduced into unsymmetrical diaryl ether originated from very trace amounts of oxygen in the reaction system. A plausible mechanism was also suggested.

Synthesis and enantioselective hydrogenation of seven-membered cyclic imines: Substituted dibenzo[b,f][1,4]oxazepines

Highly enantioselective hydrogenation of seven-membered cyclic imines, substituted dibenzo[b,f][1,4]oxazepines, was achieved, with up to 94% ee, by using the [Ir(COD)Cl]2/(S)-Xyl-C3*-TunePhos complex as the catalyst in the presence of morpholine-HCl.

Neutral alumina-K2CO3: An eco-friendly system for synthesis of diaryl ethers under microwave irradiation

Electron deficient halo benzenes undergo smoothly direct condensation with a wide range of phenols under microwave irradiation using neutral alumina as solid support to yield biaryl ethers in excellent yields.