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Relevant academic research and scientific papers

Electro-oxidative C(sp2)-H/O-H cross-dehydrogenative coupling of phenols and tertiary anilines for diaryl ether formation

The formation of diaryl ethers is generally achievedviatransition metal catalyzed etherification reactions (Ullmann, Chan-Lam, Buchwald-Hartwig) with prefunctionalized aryl halide substrates at elevated temperatures. Herein, we report a protocol for electrochemical C(sp2)-H/O-H cross-dehydrogenative coupling of phenols and tertiary anilines to synthesize diaryl ethers. The C(sp2) H/O-H coupling product can be obtained under metal- and oxidant-free conditions at room temperature in moderate to excellent yield (up to 83% yield) with high regioselectivity (>99% forpara-substitution) and with a broad substrate scope (22 examples).

Oxalohydrazide Ligands for Copper-Catalyzed C?O Coupling Reactions with High Turnover Numbers

Here, we report a class of ligands based on oxalohydrazide cores and N-amino pyrrole and N-amino indole units that generates long-lived copper catalysts for couplings that form the C?O bonds in biaryl ethers. These Cu-catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper-catalyzed coupling of aryl bromides and chlorides. This ligand also led to copper systems that catalyze the coupling of aryl chlorides with phenols and the coupling of aryl bromides and iodides with primary benzylic and aliphatic alcohols. A wide variety of functional groups including nitriles, halides, ethers, ketones, amines, esters, amides, vinylarenes, alcohols and boronic acid esters were tolerated, and reactions occurred with aryl bromides in pharmaceutically related structures.

Synthesis of diaryl ethers using an easy-to-prepare, air-stable, soluble copper(I) catalyst

We have found that bromo(triphenylphosphine)copper(I), an air-stable and soluble copper(I) complex, can be used as a catalyst in the synthesis of diaryl ethers. Using this catalyst, we have synthesized diaryl ethers from electron-rich aryl bromides and electron-rich phenols in the presence of cesium carbonate, in 17-24 h, in NMP. We also found that electron-deficient aryl bromides couple with phenols in the presence of cesium carbonate, in 6 h in NMP at 70°C, without the catalyst.