Methanol as the C₁ source: redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles

Abstract

We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazole using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher...

Aminoguanidine-Catalyzed Reductive Cyclization of o-Phenylenediamines with CO2 in the Presence of Triethoxysilane

“…The physical and spectral data were consistent with those previously reported. The physical and spectral data were consistent with those previously reported …”

Nitroarenes and nitroalkenes as potential amino sources for the synthesis of N-heterocycles

“…Recently, Nguyen et al reported an unbalanced redox condensation between o-nitroanilines and benzyl alcohols leading to benzimidazoles by using an iron-sulfur system under solvent-free conditions (Scheme 29a); 55 Li et al described a transfer of hydrogen and successive cyclization coupling reaction from o-nitroanilines and alcohols to furnish benzimidazoles using the Cu-Pd/γ-Al 2 O 3 catalytic system (Scheme 29b); 56 Wang et al developed an efficient synthesis of benzimidazoles from o-nitroanilines and alcohols via a recycled palladium-catalyzed hydrogen-transfer strategy (Scheme 29c); 57 An et al achieved an operationally simple redox coupling for the construction of benzimidazoles using 2-nitroaniline as the amino source and methanol as the carbon source under the Fe-NH 4 Cl catalytic system (Scheme 29d). 58 In 2020, Chen et al developed novel and efficient Co@NC 900 catalysts (Co nanoparticles (NPs) encapsulated in N-doped carbon nanotubes), which were investigated as a potential alternative to precious Pt-group catalysts, catalyzed hydrogenative coupling of 2-nitroaniline with benzaldehyde to construct benzoxazoles with >99% yield (Scheme 30). 59 Additionally, the Co@NC 900 catalysts can be recovered and recycled several times without any evident decrease in the activity.…”

“…Recently, Nguyen et al reported an unbalanced redox condensation between o -nitroanilines and benzyl alcohols leading to benzimidazoles by using an iron-sulfur system under solvent-free conditions (Scheme 29a); 55 Li et al described a transfer of hydrogen and successive cyclization coupling reaction from o -nitroanilines and alcohols to furnish benzimidazoles using the Cu–Pd/γ-Al 2 O 3 catalytic system (Scheme 29b); 56 Wang et al developed an efficient synthesis of benzimidazoles from o -nitroanilines and alcohols via a recycled palladium-catalyzed hydrogen-transfer strategy (Scheme 29c); 57 An et al achieved an operationally simple redox coupling for the construction of benzimidazoles using 2-nitroaniline as the amino source and methanol as the carbon source under the Fe-NH 4 Cl catalytic system (Scheme 29d). 58…”

Hexamethyldisilazane‐Mediated Synthesis of N‐Formamides, Benzimidazoles and Quinazolinones Using N,N‐Dimethylformamide as a C1 Source

“…The authors have cited additional references within the Supporting Information. [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38]…”