4.8 Article

AlCl3-Meditated CHF2 Transfer and Cyclocondensation of Difluoromethoxy Functionalized o-Phenylenediamines to Access N-Substituted Benzimidazoles

Related references

Note: Only part of the references are listed.
Article Chemistry, Multidisciplinary

Understanding the C-F Bond Activation Mediated by Frustrated Lewis Pairs: Crucial Role of Non-covalent Interactions

Jorge Juan Cabrera-Trujillo et al.

Summary: This study computationally explored the activation of a single C-F bond in di- and trifluoromethyl groups by frustrated Lewis pairs (FLPs), revealing a unique cooperative action by the FLP partners. The process proceeds through the intermediacy of a rare hypervalent species featuring a pentacoordinate carbon atom.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

Review Chemistry, Medicinal

Benzimidazoles in Drug Discovery: A Patent Review

Christine S. W. Law et al.

Summary: Benzimidazole derivatives have been widely studied in the pharmaceutical field for their wide range of pharmacological activities. This review outlines their biological effects and mechanisms of action, highlighting their potential for clinical drug development. Additionally, the study discusses novel therapeutic approaches for different target diseases using patented benzimidazoles.

CHEMMEDCHEM (2021)

Article Chemistry, Organic

Metal-Free Difunctionalization of Pyridines: Selective Construction of N-CF2H and N-CHO Dihydropyridines

Sen Zhou et al.

Summary: The reactivity of N-difluoromethylpyridinium salts is rarely explored due to their instability and low availability. However, a novel nucleophilic addition reaction has been developed to efficiently synthesize N-CF2H-dihydropyridines and N-CHO-dihydropyridines with good functional group tolerance and yields ranging from good to excellent.

ORGANIC LETTERS (2021)

Article Chemistry, Organic

FLP-Catalyzed Monoselective C-F Functionalization in Polyfluorocarbons at Geminal or Distal Sites

Richa Gupta et al.

Summary: This study presents a frustrated Lewis pair (FLP)-catalyzed monoselective C-F activation method for a range of aliphatic polyfluorocarbons with equivalent geminal and distal C-F positions, which can be further functionalized through various reactions.

ORGANIC LETTERS (2021)

Review Biochemistry & Molecular Biology

Advances in the Synthesis of Ring-Fused Benzimidazoles and Imidazobenzimidazoles

Martin Sweeney et al.

Summary: This review article provides a perspective on the synthesis of alicyclic and heterocyclic ring-fused benzimidazoles, imidazo[4,5-f]benzimidazoles, and imidazo[5,4-f]benzimidazoles. The synthesis methods are categorized and detailed, including various cyclization reactions and mechanisms. The biological activities and antitumor properties of these heterocycles are also discussed in the article.

MOLECULES (2021)

Article Chemistry, Organic

Recent synthetic methods towards the -OCHF2 moiety

Anais Loison et al.

Summary: The fluorine atom and fluorinated substituents play important roles in pharmaceutical and agrochemical active ingredients, beneficially modulating their properties. Among these, the -OCHF2 group is emerging as an interesting motif capable of forming hydrogen bonds. There is a growing need for methods to introduce this group.

TETRAHEDRON (2021)

Article Chemistry, Multidisciplinary

Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon

Lewis Caiger et al.

Summary: In this study, a method for hydroxymethylation using formaldehyde as a C1 synthon is achieved through photocatalysis and a phosphine additive. By leveraging halogen-atom transfer and capturing the O-radical, the addition reaction to formaldehyde is rendered irreversible, leading to improved efficiency and yield of the reaction.

CHEMICAL SCIENCE (2021)

Review Chemistry, Multidisciplinary

Late-stage difluoromethylation: concepts, developments and perspective

Jeroen B. I. Sap et al.

Summary: This review discusses recent advances in difluoromethylation processes, focusing on X-CF2H bond formation and the development of various difluoromethylation reagents. Metal-based methods have shown promise in transferring CF2H to C(sp(2)) sites, while Minisci-type radical chemistry has been successfully applied to difluoromethylate C(sp(2))-H bonds.

CHEMICAL SOCIETY REVIEWS (2021)

Review Chemistry, Organic

A review on synthetic approaches of benzimidazoles

Vishwajeet Amar Singh Pardeshi et al.

Summary: Benzimidazoles, a group of heterocyclic compounds, possess important pharmacological properties and play significant roles in various therapeutic areas, such as analgesics, antimicrobial agents, and antiviral drugs. They have garnered increased attention due to their outstanding bioavailability, stability, and important biological efficiency.

SYNTHETIC COMMUNICATIONS (2021)

Review Chemistry, Medicinal

Benzimidazole: A Milestone in the Field of Medicinal Chemistry

Mahesh S. Vasava et al.

MINI-REVIEWS IN MEDICINAL CHEMISTRY (2020)

Article Clinical Neurology

Daridorexant, a New Dual Orexin Receptor Antagonist to Treat Insomnia Disorder

Yves Dauvilliers et al.

ANNALS OF NEUROLOGY (2020)

Article Chemistry, Multidisciplinary

Frustrated Lewis-Pair-Meditated Selective Single Fluoride Substitution in Trifluoromethyl Groups

Dipendu Mandal et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

Article Pharmacology & Pharmacy

Rimegepant: First Approval

Lesley J. Scott

DRUGS (2020)

Review Chemistry, Organic

Progress in Benzimidazole/Benzimidazolium-Derived Supramolecular Gelators in Ion Recognition

Santanu Panja et al.

MINI-REVIEWS IN ORGANIC CHEMISTRY (2020)

Review Chemistry, Multidisciplinary

A Review on the Modern Synthetic Approach of Benzimidazole Candidate

Mohd. Faheem et al.

CHEMISTRYSELECT (2020)

Article Pharmacology & Pharmacy

Selumetinib: First Approval

Anthony Markham et al.

DRUGS (2020)

Article Chemistry, Organic

Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of D-Glucose with o-Phenylenediamines in Water

Dineshkumar Raja et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

Article Chemistry, Organic

Deprotonative Functionalization of the Difluoromethyl Group

Laura Santos et al.

ORGANIC LETTERS (2020)

Review Chemistry, Organic

A decade review of triphosgene and its applications in organic reactions

Moshood O. Ganiu et al.

TETRAHEDRON (2020)

Review Chemistry, Multidisciplinary

Recent progress on selective deconstructive modes of halodifluoromethyl and trifluoromethyl-containing reagents

Xingxing Ma et al.

CHEMICAL SOCIETY REVIEWS (2020)

Review Chemistry, Multidisciplinary

The Chemistry of CO: Carbonylation

Jin-Bao Peng et al.

Article Multidisciplinary Sciences

Chlorodifluoromethane as a C1 Synthon in the Assembly of N-Containing Compounds

Xingxing Ma et al.

ISCIENCE (2019)

Article Chemistry, Multidisciplinary

S8-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles

Shuilin Deng et al.

CHEMICAL SCIENCE (2019)

Article Biodiversity Conservation

Benzimidazole fungicides are detrimental to common farmland ants

Petr Heneberg et al.

BIOLOGICAL CONSERVATION (2018)

Article Chemistry, Multidisciplinary

The Difluoromethyl Group as a Masked Nucleophile: A Lewis Acid/Base Approach

Jacob B. Geri et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

Review Chemistry, Multidisciplinary

Recent advances in organic synthesis with CO2 as C1 synthon

Gaoqing Yuan et al.

CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY (2017)

Article Chemistry, Organic

Ruthenium-Catalyzed Urea Synthesis Using Methanol as the C1 Source

Seung Hyo Kim et al.

ORGANIC LETTERS (2016)

Article Chemistry, Organic

Direct Nucleophilic Difluoromethylation of Carbonyl Compounds

Zuyong Deng et al.

ORGANIC LETTERS (2016)

Article Chemistry, Organic

Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction

Rakesh H. Vekariya et al.

ORGANIC LETTERS (2016)

Article Chemistry, Multidisciplinary

Frustrated Lewis Pair Chemistry: Development and Perspectives

Douglas W. Stephan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Review Chemistry, Medicinal

Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review

Geeta Yadav et al.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2015)

Article Chemistry, Multidisciplinary

Frustrated Lewis Pairs

Douglas W. Stephan

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

Article Chemistry, Organic

Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol

Hashim F. Motiwala et al.

ORGANIC LETTERS (2015)

Review Chemistry, Medicinal

Benzimidazole: a promising pharmacophore

Kamal Shah et al.

MEDICINAL CHEMISTRY RESEARCH (2013)

Article Chemistry, Organic

New electrophilic difluoromethylating reagent

G. K. Surya Prakash et al.

ORGANIC LETTERS (2007)

Article Chemistry, Multidisciplinary

Facile heterolytic cleavage of dihydrogen by phosphines and boranes

Gregory C. Welch et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

Article Chemistry, Multidisciplinary

Rapid intramolecular heterolytic dihydrogen activation by a four-membered heterocyclic phosphane-borane adduct

Patrick Spies et al.

CHEMICAL COMMUNICATIONS (2007)

Article Multidisciplinary Sciences

Reversible, metal-free hydrogen activation

Gregory C. Welch et al.

SCIENCE (2006)