895582-17-9

Upstream product

• 4857-06-1 2-chloro-1H-benzoimidazole 
• 40400-13-3 2-Iodobenzyl bromide 
• 4622-38-2 2-iodobenzyliodide 

Downstream Products

• 1030593-59-9 1-(2-iodobenzyl)-2-thiobenzimidazole 
• 248-72-6 11H-benzo[4,5]imidazo[2,1-a]isoindole 
• 895582-08-8 4-({1-[(2-iodophenyl)methyl]-1H-benzo[d]imidazol-2-yl}sulfanyl)benzene-1-carboxylic acid 

Relevant academic research and scientific papers

Intramolecular homolytic aromatic substitution of alkyl 2-benzimidazolyl sulfones as a means of entry into alkyl radicals for organic synthesis

The intramolecular radical aromatic substitution of heteroaryl sulfones by tethered aryl radicals has been investigated as a source of alkyl radicals. The 1-(2-iodobenzyl)benzimidazole-2-sulfonyl system was found to be the most effective, while a tetrazole-based system did not undergo the desired radical aromatic substitution at all. Application of the benzimidazole-based system to the generation of alkyl radical and their subsequent use in radical cyclizations was demonstrated.

Aromatic homolytic substitution using solid phase synthesis

Solid phase synthesis has been used to carry out intramolecular aromatic homolytic substitution with benzoimidazole precursors. The protocol attaches the radical precursors to the resins via the radical leaving groups (in the aromatic homolytic substitution). When the radical reactions are complete, the leaving group, unaltered starting material and reduced uncylised products remain attached to the resin, which facilitates easy separation of the cyclised products. Novel use of focussed microwave irradiation in solid phase radical reactions drastically shortens the reactions times. Tributylgermanium hydride has been used to replace the toxic and troublesome tributyltin hydride in the radical reactions.