248-72-6

Upstream product

• 87-41-2 2-benzofuran-1(3H)-one 
• 39145-59-0 o-phenylenediamine hydrochloride 
• 7664-93-9 sulfuric acid 
• 858442-03-2 [2-(2-amino-phenyl)-4-oxo-1,2,3,4-tetrahydro-phthalazin-1-yl]-acetic acid 
• 7647-01-0 hydrogenchloride 
• 895582-10-2 methyl 4-({1-[(2-iodophenyl)methyl]-1H-benzo[d]imidazol-2-yl}sulfanyl)benzene-1-carboxylate 
• 895582-17-9 2-chloro-1-[(2-iodophenyl)methyl]-1H-benzo[d]imidazole 
• 895582-08-8 4-({1-[(2-iodophenyl)methyl]-1H-benzo[d]imidazol-2-yl}sulfanyl)benzene-1-carboxylic acid 
• 4857-06-1 2-chloro-1H-benzoimidazole 
• 4622-38-2 2-iodobenzyliodide 
• 4981-92-4 1-benzylbenzimidazole 
• 1418363-64-0 2-iodo-1-trityl-1H-benzimidazole 
• 27692-04-2 2-iodo-1H-benzo[d]imidazole 
• 312631-73-5 1-benzyl-2-iodo-1H-benzo[d]imidazole 

Downstream Products

• 2717-05-7 1,2-benzoylenebenzimidazole 
• 16529-06-9 2-(2-carboxyphenyl)benzimidazole 

Relevant academic research and scientific papers

Copper(I)-catalyzed intramolecular direct C-arylation of azoles with aryl bromides

A concise route to access 5H-imidazo[2,1-a]isoindole heterofused compounds by copper(I)-catalyzed intramolecular coupling of non-activated aryl bromides with azoles is reported. With CuI as catalyst, 1,10-phenanthroline as ligand, and K3PO4 as base, the reactions of 1-(2-bromobenzyl)-1H- imidazoles in DMF/o-xylene (1:1, V:V) at 145°C afford the corresponding substituted 5H-imidazo[2,1-a]isoindoles in high yields via intramolecular C-arylation. A concise route to access 5H-imidazo[2,1-a]isoindole heterofused compounds by copper(I)-catalyzed intramolecular coupling of non-activated aryl bromides with azoles is reported for the first time. With CuI as catalyst, 1,10-phenanthroline as ligand, and K3PO4 as base, the reactions of 1-(2-bromobenzyl)-1H-imidazoles in DMF/o-xylene (1:1, V:V) at 145°C afford the corresponding substituted 5H-imidazo[2,1-a]isoindoles in high yields via intramolecular C-arylation. Copyright

1,1-Hydroboration of Fused Azole-Isoindole Analogues as an Approach for Construction of B,N-Heterocycles and Azole-Fused B,N-Naphthalenes

Three isoelectronic analogues of pyrido[2,1-a]isoindole have been found to undergo a facile 1,1-hydroboration with HBMes2 borane, which provides a new and convenient method for the synthesis of B,N-heterocycles 1a-3a in high yields. Compounds 1a-3a can undergo photoelimination upon irradiation at 300 nm, generating heterocycle-fused B,N-naphthalene molecules 1b-3b, which display distinct yellow-green and blue fluorescent colors, respectively. Compound 1a undergoes thermal elimination, producing 1b at 280°C, while compound 2a only undergoes partial elimination, forming 2b at 320°C. Compound 3a is thermally stable up to 320°C.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

Synthesis of benzimidazoles via iridium-catalyzed acceptorless dehydrogenative coupling

Iridium-catalyzed acceptorless dehydrogenative coupling of tertiary amines and arylamines has been developed. A number of benzimidazoles were prepared in good yields. An iridium-mediated C-H activation mechanism is suggested. This finding represents a novel strategy for the synthesis of benzimidazoles.

Dual Catalysis in Domino N-Benzylation/Intramolecular C-H Arylation: Regio- and Chemoselective Synthesis of Annelated Nitrogen Heterocycles

A general method has been developed for the synthesis of fused nitrogen heterocycles by using a domino N-benzylation/C-H arylation reaction sequence. The details and yields of the domino process were compared with those of the two-step literature protocol

Metal-free TEMPO-promoted C(sp3)-H amination to afford multisubstituted benzimidazoles

An efficient TEMPO-air/cat. TEMPO-O2 oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp3 C-H and free N-H of readily available N1-benzyl/alkyl-1,2-phenylenediamines.

Intramolecular arylation of benzimidazoles via Pd(II)/Cu(I) catalyzed cross-dehydrogenative coupling

Electron poor benzimidazole substrates were arylated via an intramolecular cross-dehydrogenative coupling (CDC) reaction. These CDC reactions were catalyzed by a Pd(II)/Cu(I) catalyst system, capable of producing moderate yields on a large library of substrates. The substrate scope consisted of tethered arene-benzimidazoles that upon coupling, produced a fused polycyclic motif.

Metal-free construction of tricyclic or tetracyclic compounds - Acid-promoted synthesis of benzo[4,5]imidazo[2,1-a]isoindole and 1,2-dialkyl-2,3-dihydrobenzimidazoles

An environmental friendly, efficient, and easy to operate strategy for synthesizing of benzo[4,5]imidazo[2,1-a]isoindole and 1,2-dialkyl-2,3- dihydrobenzimidazoles via acid-promoted coupling of dialdehyde and o-diaminobenzene under metal-free conditions is described. A series of products were generated in good yields under mild conditions.

Access to aromatic ring-fused benzimidazoles using photochemical substitutions of the benzimidazol-2-yl radical

Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution onto the benzimidazole-2-position.

Access to aromatic ring-fused benzimidazoles using photochemical substitutions of the benzimidazol-2-yl radical

Photochemical five-, six-, and seven-membered cyclizations from 2-iodo-1-(ω-arylalkyl)-1H-benzimidazoles are described. This method of producing aromatic ring-fused benzimidazoles is significantly more efficient than literature radical protocols using chemical initiators, although 2-iodo-1-(ω-pyridin-2-ylalkyl)-1H-benzimidazoles preferentially undergo a nucleophilic ipso-substitution onto the benzimidazole-2-position. Georg Thieme Verlag Stuttgart - New York.