958-96-3

Upstream product

• 98-95-3 nitrobenzene 
• 7664-93-9 sulfuric acid 
• 7722-84-1 dihydrogen peroxide 
• 31268-20-9 bromomethyl phenyl sulfoxide 
• 13331-27-6 m-nitrobenzene boronic acid 
• 1104877-48-6 4-bromo-2-(2-iodo-phenoxy)methyl-1-(prop-1-ynyl)benzene 
• 80281-73-8 N-tert-Butyl-3-diisopropylamino-N'-(4-nitro-phenyl)-propionamidine 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 2865-17-0 m-nitrophenylmercury(II) chloride 
• 626-00-6 1,3-Diiodobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 24163-36-8 3,3'-dinitrodiphenyliodonium bromide 
• 645-00-1 m-iodonitrobenzene 
• 95919-09-8 2,2''-diiodo-[1,1':4',1'']terphenyl 

Downstream Products

• 128923-93-3 1‐(3‐methoxyphenyl)‐3‐nitrobenzene 
• 31835-64-0 3-amino-3'-nitrobiphenyl 
• 136905-61-8 N³,N³,N^3',N^3'-Tetrakis-(4-methoxy-phenyl)-biphenyl-3,3'-diamine 
• 106323-83-5 3,4,3'-Trinitro-biphenyl 

Relevant academic research and scientific papers

An Active Palladium Colloidal Catalyst for the Selective Oxidative Heterocoupling of (Hetero)Aryl Boronic Acids

A highly selective oxidative heterocoupling protocol for (hetero)aryl boronic acids with an active palladium colloidal catalyst was developed. The judicious choice of electronically different aryl boronic acids made possible such couplings under mild conditions, with air as oxidant, while embracing a wide substrate scope. This successful approach further allowed the development of a unique one-pot sequential oxidative heterocoupling/Suzuki–Miyaura cross-coupling tandem process for accessing substituted terphenyls.

Copper(i)-catalyzed amidation reaction of organoboronic esters and isocyanates

A simple and efficient methodology for the preparation of amides from easily available organoboronic esters and isocyanates has been accomplished using a ligand-free copper(i) catalyst. The reaction system demonstrated a broad substrate scope and provided convenient access to a wide variety of secondary amides.

A deacetylation-diazotation-coupling sequence: Palladium-catalyzed C-C bond formation with acetanilides as formal leaving groups

Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki crosscoupling reactions, and a Pd-catalyzed [2+2+1] cycloaddition hav

Palladium(II)-catalyzed coupling of electron-deficient arenes via C-H activation

Homocoupling and cross-coupling of electron-deficient arenes, including nitrobenzene, (trifluoromethyl)benzene, ethyl benzoate, etc., have been developed to afford biaryls using a catalytic system of Pd(OAc) 2/trifluoroacetic acid (TFA)/O2 or K2S 2O8. The crucial step is to tune the concentrations of arenes and the loading of TFA carefully to enhance the reaction rates and the selectivity of these couplings involving dual C-H activation.

Suzuki-Miyaura reactions of the soluble guanylate cyclase inhibitor NS2028: A non-product specific route to C-8 substituted analogues

Both soluble guanylate cyclase (sGC) inhibitors ODQ 1 and NS2028 2 are synthesized via improved protocols. In the former case treating 3,4-dihydroquinoxalin-2(1H)-one oxime 8, which can be prepared in two steps from 1,2-benzenediamine, with 1,1′-carbonyldiimidazole (CDI) gives the dihydro-ODQ 10 that in the presence of KMnO4 oxidises to give ODQ 1 in an overall yield of 46% starting from 1,2-benzenediamine. In the latter case, the synthesis affords NS2028 2 from 2-amino-4-bromophenol 3 in three steps with an overall yield of 85% and avoids the need for chromatography. Furthermore, Suzuki-Miyaura reaction conditions are described that enable the preparation of 8-aryl and 8-heteroaryl derivatives of NS2028 directly from NS2028 2. Finally, demethylation of the 8-(methoxyphenyl) substituted analogues afforded the 8-(hydroxyphenyl) derivatives 40-42. All new products are fully characterised.

Homocoupling of arylboronic acids catalyzed by CuCl in air at room temperature

Homocoupling of arylboronic acids has been successfully carried out by using the inexpensive simple copper salt CuCl as the catalyst in methanol to obtain symmetric biaryls in good to excellent yields. The reaction proceeds with a CuCl loading of 2 mol-% under extremely mild conditions: in air, at room temperature, without the need of any additives such as base, oxidant, or ligand. A simple and efficient CuCl-catalyzed homocoupling of arylboronic acids for the synthesis of symmetrical biaryls is described. The homocoupling reaction takes place with a catalyst loading of at 2 mol-% in economical and easily handled methanol and under extremely mild conditions: in air, at room temperature, without any additives such as base, oxidant, or ligand. Copyright

Preparation of unsymmetrical biaryls by pd(II)-catalyzed cross-coupling of aryl iodides

The Ullmann homo-and cross-couplings of aryl iodides are carried out to afford symmetrical and unsymmetrical biaryls in moderate to good yields in a catalytic system of Pd(OAc)2/K2CO3/MeCOEt. The high selectivity of unsymmetrical biaryl products in cross-couplings mainly depends on the reactivity difference between two iodoarene substrates and their employed ratios.

Development of an efficient palladium-catalyzed intramolecular carbometalation reaction for the synthesis of a dibenzoxapine containing tetra-substituted exocyclic alkene

A practical and scaleable synthesis of (Z)-3-(1-(8-bromodiben-zo[b,e] oxepin-ll(6H)-ylidene) ethyl) aniline hydrochloride (1 *HC1), a key intermediate in the synthesis of a selective nuclear hormone receptor modulator, is described. The target compound is

Palladium-catalyzed cross-coupling of five-membered heterocyclic silanolates

(Chemical Equation Presented) The preparation of π-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables: (1) identification of stable, isolable alkali metal silanolates, (2) identification of conditions for preformation and isolation of silanolate salts, (3) judicious choice in the palladium catalyst/ligand combination, and (4) selection of the protecting group on the nitrogen of indole. It was found that the alkali metal silanolates, either isolated or formed in situ, offered a significant rate enhancement and broader substrate scope over the use of silanols activated by Bronsted bases such as NaOt-Bu. In addition, the optimized conditions for the cross-coupling of 2-indolylsilanolates were readily applied to the cross-coupling of 2-pyrrolyl-, 2-furyl-, and 2-thienylsilanolates.

Copper(I)-catalysed homo-coupling of aryldiazonium salts: synthesis of symmetrical biaryls

Copper(I) triflate acts as an efficient stoichiometric reagent for the homo-coupling of aryldiazonium salts bearing electron-withdrawing group(s), to yield symmetrical biaryls in acetonitrile under mild reaction conditions. Aryldiazonium salts bearing electron-donating groups undergo the reaction by using catalytic amounts of a copper complex prepared in situ from copper(II) triflate and 2,2′-bipyridine with metallic copper as an ultimate reductant.