4783-69-1

Upstream product

• 109-04-6 2-bromo-pyridine 
• 106-48-9 4-chloro-phenol 
• 4783-68-0 2-phenoxypyridine 
• 142-08-5 2-Pyridone 
• 109-09-1 2-chloropyridine 
• 5029-67-4 2-iodopyridine 

Downstream Products

• 1541842-22-1 (2E,2′E)-diethyl 3,3′-(5-chloro-2-(pyridin-2-yloxy)-1,3-phenylene)diacrylate 
• 195062-61-4 4-chlorophenylboronic acid pinacol ester 
• 28355-36-4 2-(2,4,6-trichlorophenoxy)pyridine 
• 22082-98-0 2-(4-chlorophenyl)naphthalene 

Relevant academic research and scientific papers

Ruthenium-Catalyzed meta-CAr–H Bond Difluoroalkylation of 2-Phenoxypyridines

A ruthenium-catalyzed meta-selective CAr–H bond difluoroalkylation of 2-phenoxypyridine using 2-bromo-2,2-difluoroacetate has been developed. Mechanistic studies indicated that this difluoroalkylation might involve a radical process. Furthermore, a new method is reported for the synthesis of 2-(meta-difluoroalkylphenoxy)pyridine derivatives, which are present in many pharmaceuticals and other functional compounds.

A directing group-assisted ruthenium-catalyzed approach to access: Meta -nitrated phenols

meta-Selective C-H nitration of phenol derivatives was developed using a Ru-catalyzed σ-activation strategy. Cu(NO3)2·3H2O was employed as the nitrating source, whereas Ru3(CO)12 was found to be the most suitable metal catalyst for the protocol. Mechanistic studies suggested involvement of an ortho-CAr-H metal intermediate, which promoted meta-electrophilic aromatic substitution and silver-assisted free-radical pathway.

N - And O -arylation of pyridin-2-ones with diaryliodonium salts: Base-dependent orthogonal selectivity under metal-free conditions

Metal-free N- and O-arylation reactions of pyridin-2-ones as ambident nucleophiles have been achieved with diaryliodonium salts on the basis of base-dependent chemoselectivity. In the presence of N,N-diethylaniline in fluorobenzene, pyridin-2-ones were very selectively converted to N-arylated products in high yields. On the other hand, the O-arylation reactions smoothly proceeded with the use of quinoline in chlorobenzene, leading to high yields and selectivities. In these methods, a variety of pyridin-2-ones in addition to pyridin-4-one and a set of diaryliodonium salts were accepted as suitable reaction partners.

Identification of an Oxalamide Ligand for Copper-Catalyzed C?O Couplings from a Pharmaceutical Compound Library

A typical pharmaceutical compound library is stocked with molecular diversity and could provide a platform for the discovery of new ligand structures. Herein, we describe the use of this approach in combination with high throughput screening to identify N,N’-bis(thiophene-2-ylmethyl)oxalamide as a ligand that is generally effective for copper-catalyzed C?O cross-couplings to prepare both biarylethers as well as phenols under mild conditions.

Chromium-Catalyzed Regioselective Kumada Arylative Cross-Coupling of C(aryl)-O Bonds with a Traceless Activation Strategy

We report here the chromium-catalyzed regioselective Kumada arylative cross-coupling of C(aryl)-O bonds at ambient temperature. By using a simple and low-cost chromium(II) chloride salt as a precatalyst, accompanied by a 2-pyridyl ligation, the catalytic cleavage and arylative coupling of C(aryl)-O bonds were achieved with a traceless activation strategy, overcoming the regioselectivity obstacle when several C-O bonds coexist in the Kumada coupling system.

Regioselective C-H chlorination: Towards the sequential difunctionalization of phenol derivatives and late-stage chlorination of bioactive compounds

We have developed a protocol for the auxillary directed C-H chlorination of phenol derivatives using catalytic amounts of palladium acetate that is amenable to the late-stage chlorination of diflufenican and estrone. The 2-pyridine group allows for a highly efficient palladium-catalyzed chlorination and sequential ortho C-H functionalization reaction of phenol derivatives to produce a variety of symmetrical and unsymmetrical 2,4,6-trisubstituted phenols.

Synthesis of m-Alkylphenols via a Ruthenium-Catalyzed C-H Bond Functionalization of Phenol Derivatives

The first example of the synthesis of m-alkylphenols via a ruthenium-catalyzed CAr-H bond functionalization of phenol derivatives with sec/tert-alkyl bromides is reported. Mechanistic studies indicated that the m-CAr-H bond alkylation may involve a radical process and that a six-membered ruthenacycle complex was the active catalyst. Moreover, this approach can provide an expedited strategy for the atom-/step-economical synthesis of many noteworthy pharmaceuticals and other functional molecules.

Rhodium-catalyzed borylation of aryl 2-pyridyl ethers through cleavage of the carbon-oxygen bond: Borylative removal of the directing group

The rhodium-catalyzed reaction of aryl 2-pyridyl ethers with a diboron reagent results in the formation of arylboronic acid derivatives via activation of the C(aryl)-O bonds. The straightforward synthesis of 1,2-disubstituted arenes was enabled through catalytic ortho C-H bond functionalization directed by the 2-pyridyloxy group followed by substitution of this group with a boryl group. Several control experiments revealed that the presence of a sp2 nitrogen atom at the 2-position of the substrate and the use of a boron-based reagent were crucial for the activation of the relatively inert C(aryl)-O bond of aryl 2-pyridyl ethers.

Chemoselective and ligand-free synthesis of diaryl ethers in aqueous medium using recyclable alumina-supported nickel nanoparticles

An economical and eco-compatible ligand-free protocol for the synthesis of diaryl ethers has been developed using easily accessible alumina-supported nickel nanoparticles as a stable recyclable heterogeneous catalyst in aqueous medium along with a surfactant (SDS) and a mild base (K2CO3). Various sensitive functional groups like allyl, alkoxycarbonyl, formyl, oxo, chloro, bromo, amine and nitro were tolerated in the aforesaid method. Excellent chemoselectivity was demonstrated through competition experiments.

Palladium-catalyzed oxidative olefination of phenols bearing removable directing groups under molecular oxygen

An efficient Pd(II)-catalyzed oxidative olefination of phenols bearing removable directing groups with molecular oxygen as the sole oxidant has been developed. This reaction protocol provides an efficient and robust synthetic tool for the synthesis of o-alkenyl phenols under mild conditions.