79365-05-2

Upstream product

• 5720-05-8 4-methylphenylboronic acid 
• 612-24-8 o-nitrobenzonitrile 
• 106-44-5 p-cresol 
• 873-32-5 2-Chlorobenzonitrile 
• 4387-36-4 2-iodobenzonitrile 
• 2042-37-7 o-cyanobromobenzene 
• 394-47-8 2-fluorobenzonitrile 
• 209190-33-0 2-(4-methylphenoxy)benzophenone O-methyloxime 

Downstream Products

• 1236842-06-0 N-triphenylmethyl-5-[2-(4'-methylphenoxy)phenyl]tetrazole 
• 1412761-21-7 trimethyl(2-(p-tolyloxy)phenyl)silane 
• 1412761-53-5 trimethyl(5-methyl-2-phenoxyphenyl)silane 
• 607-88-5 p-tolyl 2-hydroxybenzoate 
• 21905-69-1 2-(4-methylphenoxy)-benzoic acid 
• 922731-22-4 2,2-dimethyl-1-(2-p-tolyloxyphenyl)propan-1-one 

Relevant academic research and scientific papers

2,4-Diaminotriazines as anti-infective agents

Triazines are scaffolds of interest to medicinal chemists as they have a wide variety of pharmacological activities. Molecules with the triazine moiety have been explored extensively for their anti-infective potential. In this paper, we report a series of

Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation

A conceptually new and synthetically valuable radical Smiles rearrangement reaction is reported under undivided electrolytic conditions. This protocol employs an entirely new strategy for the electrochemical radical Smiles rearrangement. Remarkably, an amidyl radical generated from the cleavage of the N-O bond under reductive electrolytic conditions plays a crucial role in this transformation. Various hydroxylamine derivatives bearing different substituents are suitable in this electrochemical transformation, furnishing the corresponding amides in up to 86% yield.

Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings

Diaryl formation is achieved by coupling phenols and (hetero)aryl halides under the catalysis of CuI/N,N′-bis(2-phenylphenyl) oxalamide (BPPO) or CuI/N-(2-phenylphenyl)-N′-benzyl oxalamide (PPBO) at 90 °C using DMF or MeCN as the solvent. Only 0.2-2 mol % CuI and ligand are required for complete conversion, which represents the lowest catalytic loadings for a general Cu/ligand-catalyzed diaryl ether formation.

Efficient Aryl Migration from an Aryl Ether to a Carboxylic Acid Group To Form an Ester by Visible-Light Photoredox Catalysis

We have developed a highly efficient aryl migration from an aryl ether to a carboxylic acid group through retro-Smiles rearrangement by visible-light photoredox catalysis at ambient temperature. Transition metals and a stoichiometric oxidant and base are avoided in the transformation. Inspired by the high efficiency of this transformation and the fundamental importance of C?O bond cleavage, we developed a novel approach to the C?O cleavage of a biaryl ether to form two phenolic compounds, as demonstrated by a one-pot, two-step gram-scale reaction under mild conditions. The aryl migration exhibits broad scope and can be applied to the synthesis of pharmaceutical compounds, such as guacetisal. Primary mechanistic studies indicate that the catalytic cycle occurs by a reductive quenching pathway.

CuI/oxalamide catalyzed couplings of (hetero)aryl chlorides and phenols for diaryl ether formation

Couplings between (hetero)aryl chlorides and phenols can be effectively promoted by CuI in combination with an N-aryl-N′-alkyl-substituted oxalamide ligand to proceed smoothly at 120 °C. For this process, N-aryl-N′-alkyl-substituted oxalamides are more effective ligands than bis(N-aryl)-substituted oxalamides. A wide range of electron-rich and electron-poor aryl and heteroaryl chlorides gave the corresponding coupling products in good yields. Satisfactory conversions were achieved with electron-rich phenols as well as a limited range of electron-poor phenols. Catalyst and ligand loadings as low as 1.5 mol % are sufficient for the scaled-up variants of some of these reactions. Aryl and alkyl: N-Aryl-N′-alkyl-substituted oxalamide ligands promote the CuI catalyzed coupling of (hetero)aryl chlorides and phenols at 120 °C more effectively than bis(N-aryl)-substituted oxalamides. A wide range of electron-rich and electron-poor aryl and heteroaryl chlorides were converted into the corresponding coupling products in good yields.

First palladium-catalyzed denitrated coupling reaction of nitroarenes with phenols

The first palladium-catalyzed protocol for the denitrated coupling reaction of nitroarenes with phenols has been developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. The cyclopalladated ferrocenylimine (catalyst Ic) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol%) and short reaction time (2 h). The efficiency of this reaction was demonstrated by its compatibility with a range of groups. Moreover, the rigorous exclusion of air or moisture was not required in these transformations. Copyright

A 2,2′-bipyridine-palladacycle catalyzed the coupling of arylboronic acids with nitroarenes

A novel palladium-catalyzed protocol for the synthesis of diaryl ethers derivatives has been developed. In the presence of 2,2′-bipyridine- cyclopalladated ferrocenylimine complex (Cat. Ic), diaryl ethers were selectively generated by adjusting reaction parameters through the coupling of arylboronic acids and nitroarenes with yields ranging from poor to good. The efficiency of this reaction was demonstrated by its compatibility with a range of groups. Moreover, the rigorous exclusion of air or moisture was not required in these transformations.

1,5-Migration of rhodium via C-H bond activation in catalytic decyanative silylation of nitriles

Unprecedented aryl-to-aryl 1,5-rhodium migration is involved in decyanative silylation of aryl cyanides bearing a tethered arene. The 1,5-migration proceeds through remote C-H bond activation. 1,5-Migration also occurs in other rhodium-catalyzed reactions, including borylation and oxidative Mizoroki-Heck reactions.

A study of the gas-phase interconversion of 1-(2-aryloxyphenyl)-alkaniminyl and 2-(aryliminomethyl)phenoxyl radicals

Flash vacuum pyrolysis of the allyl ethers 9-11 and of the oxime ethers 15-17 at 650°C (5 × 10-2-5 × 10-3 Torr) generates 2-(aryliminomethyl)phenoxyl radicals 4 and 1-(2-aryloxyphenyl)alkaniminyl radicals 5 respectively which can interconvert via a spirodienyl radical leading to common products which are generally isolated in low to moderate yield. The iminyls 5 normally undergo β-cleavage leading to nitriles (e.g. 21) and/or to benzofurans (e.g. 22) after cyclisation. The phenoxyls 4 show more complex behaviour dominated by hydrogen abstraction processes leading to products such as phenols (e.g. 32), the indole 27 or phenanthridines 34 and 35.

Angiotensin II receptor antagonists

Compounds are disclosed having the formula: STR1 The compounds of the invention are angiotensin II receptor antagonists.