Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

Benzimidazoles are important -heteroaromatic compounds with various biological activities and pharmacological applications. Herein, we present the first iron-catalyzed selective synthesis of 1,2-disubstituted benzimidazoles acceptorless dehydrogenative coupling of primary alcohols with aromatic diamines. The tricarbonyl (η-cyclopentadienone) iron complex catalyzed dehydrogenative cyclization, releasing water and hydrogen gas as by-products. The earth abundance and low toxicity of iron metal enable the provision of an eco-friendly and efficient catalytic method for the synthesis of benzimidazoles.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7317090PMC
http://dx.doi.org/10.3389/fchem.2020.00429DOI Listing

Publication Analysis

Top Keywords

acceptorless dehydrogenative
8
dehydrogenative coupling
8
alcohols aromatic
8
aromatic diamines
8
selective synthesis
8
synthesis 12-disubstituted
8
12-disubstituted benzimidazoles
8
iron-catalyzed acceptorless
4
coupling alcohols
4
diamines selective
4

Similar Publications

The Friedländer quinoline synthesis represents a fundamental method for the construction of quinoline derivatives, a versatile class of heterocyclic compounds widely prevalent in pharmaceuticals and materials science. This synthesis traditionally involves the condensation of 2-aminoaryl ketones with carbonyl compounds, typically ketones or aldehydes, in the presence of an acid or base under reflux conditions. However, recent advancements have highlighted indirect approaches (starting from 2-aminobenzyl alcohol) to achieve the same quinoline framework, offering distinct advantages in selectivity, substrate scope, and functional group tolerance.

View Article and Find Full Text PDF

In this study, we report NNN pincer bis-imino pyridine-supported copper(II) catalysts for the sustainable, eco-friendly, and practical multi-component synthesis (MCS) of pyrazolines and pyrimidines driven by the acceptorless dehydrogenation of benzyl alcohols. Herein, we synthesize and characterize two well-defined phosphine-free NNN pincer-supported copper(II) complexes, C1 and C2, using IR, UV-vis, HRMS, and single-crystal XRD. Utilizing these complexes, we develop the first multi-component synthetic route for 1,3,5-trisubstituted pyrazolines (TriPyz) from the dehydrogenative coupling of renewable benzyl alcohols and aromatic ketones with phenyl hydrazine, generating ecologically benign HO and H as side products.

View Article and Find Full Text PDF

In this report, we present a sustainable, eco-friendly, practical, and cost-effective one-pot three-component reaction for the synthesis of a diverse library of highly substituted pyrimidines from amidines, primary alcohols, and aromatic ketones, catalyzed by a cobalt(III) complex. The well-defined cobalt(III) complex [Co(III)BPMAP-O]ClO is derived from a redox-active phosphine-free, pentadentate mono-carboxamide ligand (BPMAP-H), and is formed in situ from various cobalt(II) sources, including CoCl·6HO, CoBr, Co(NO)·6HO, Co(OAc)·4HO via oxygen activation. Using aromatic ketones and benzyl alcohols, a wide range of 2,4,6-trisubstituted pyrimidines (TriPym) and 2,4,5,6-tetrasubstituted pyrimidines (TetraPym) were synthesized (119 examples) in isolated yields of up to 93%.

View Article and Find Full Text PDF

Liquid organic hydrogen carriers (LOHCs) offer an attractive strategy for efficient hydrogen storage and release, thereby facilitating the effective use of hydrogen as a carbon-neutral energy carrier. The advancement of LOHC technology is highly dependent on the innovation of the catalysts. Herein, based on a strategy combining rigidity and flexibility in a single molecular catalyst, a novel class of PNP-pincer ligands, called long-short-arm acridine ligands, and their Ru complexes have been developed and successfully used in the LOHC system based on ethylene glycol (EG).

View Article and Find Full Text PDF

We systematically investigated how the position of the methyl group in methylpiperidine/methylpyridine (MPI/MPY) pairs governs its acceptorless dehydrogenation reactivity through three perspectivesthermodynamics, kinetics, and adsorption. Among the MPI isomers, 2-MPI shows the highest conversion of 97.5% and a fast reaction rate of 1.

View Article and Find Full Text PDF