51263-25-3

Upstream product

• 694-59-7 pyridine N-oxide 
• 874-69-1 N-phenylacetimidoyl chloride 
• 103-84-4 Acetanilid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 6631-37-4 2-(phenylamino)pyridine 
• 504-29-0 2-aminopyridine 
• 108-86-1 bromobenzene 
• 75-36-5 acetyl chloride 

Relevant academic research and scientific papers

One-Pot Protocol to Synthesize 2-Aminophenols from Anilines via Palladium-Catalyzed C-H Acetoxylation

This paper describes a facile one-pot protocol to synthesize 2-aminophenol derivatives via a palladium-catalyzed C-H acetoxylation strategy with 5-nitropyrimidine as a directing group (DG), which can be easily preinstalled and readily removed under mild condition after the coupling. In addition, the transformation is operationally simple, has high functional group tolerance, and is amenable to gram-scale. Moreover, several examples were shown that introduction/removal of 5-nitropyrimidine and the C-H oxylation sequence could be integrated in one pot.

A VERSATILE LIGAND FOR PALLADIUM-CATALYZED META-C-H FUNCTIONALIZATIONS

A class of mono-protected 3-amino-2- hydroxypyridine (MPAHP) ligands that enable the meta- C-H arylation of anilines, phenols, phenylacetic acids, and biologically relevant heterocyclic compounds using norbornene as a transient mediator is disclosed. The applicability of this meta-arylation methodology in the pharmaceutical industry is illustrated for heteroaryl substrates and heteroaryl iodide coupling partners, a feat made possible by using the MPAHP ligand. The enabling nature of MPAHP ligands to achieve other meta-C-H functionalization processes is also illustrated by the development of a meta-C-H amination reaction and a meta-C-H alkynylation reaction.

Ligand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles

Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative. The first steps toward a silver-free protocol for this reaction are also demonstrated.

Direct dehydrative n-pyridinylation of amides

Electrophilic activation of secondary amides with trifluo-romethanesulfonic anhydride in the presence of 2-fluoropy-ridine followed by introduction of a pyridine N-oxide derivative and warming affords the corresponding N-pyridi-nyl tertiary amide derivati

A mild method for the formation and in situ reaction of imidoyl chlorides: conversion of pyridine-1-oxides to 2-aminopyridine amides.

[reaction: see text] A mild, practical, one-pot method for the generation of imidoyl chlorides and their subsequent in situ reaction with pyridine-1-oxides is described. The imidoyl chlorides were formed from the reaction of secondary amides with a stoich