Copper containing nanosilica thioalated dendritic material: A recyclable catalyst for synthesis of benzimidazoles and benzothiazoles

Zakeri, Maryam; Moghadam, Majid; Mirkhani, Valiollah; Tangestaninejad, Shahram; Mohammadpoor‐Baltork, Iraj; Pahlevanneshan, Zari

doi:10.1002/aoc.3937

Cited by 24 publications

(9 citation statements)

References 76 publications

(60 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In addition to oxidation, thiol FSs could undergo other significant chemical modifications as described here . Thiol FS has undergone a nucleophilic substitution with chloroethanol.…”

Section: Conventional Fss: Types and Their Chemical Modificationsmentioning

confidence: 99%

“…Thiolated silica dendrite is prepared through the nucleophilic substitution involving thiol FS and 1,3,5‐benzenetricarbonyl trichloride. The growth of the dendrite is maintained and controlled by carrying out the repeated nucleophilic substitution reactions using 1,3,5‐benzenetricarbonyl trichloride and 1,2‐ethanedithiol . A. Nakamizu et al.…”

Section: Conventional Fss: Types and Their Chemical Modificationsmentioning

confidence: 99%

See 1 more Smart Citation

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Antony

Marimuthu

Yang

et al. 2019

The Chemical Record

View full text Add to dashboard Cite

Heterogeneous catalysis plays a key role in promoting green chemistry through many routes. The functionalizable reactive silanols highlight silica as a beguiling support for the preparation of heterogeneous catalysts. Metal active sites anchored on functionalized silica (FS) usually demonstrate the better dispersion and stability due to their firm chemical interaction with FSs. Having certain functional groups in structure, FSs can act as the useful catalysts for few organic reactions even without the need of metal active sites which are termed as the covetous reusable organocatalysts. Magnetic FSs have laid the platform where the effortless recovery of catalysts is realized just using an external magnet, resulting in the simplified reaction procedure. Using FSs of multiple functional groups, we can envisage the shortened reaction pathway and, reduced chemical uses and chemical wastes. Unstable bio‐molecules like enzymes have been stabilized when they get chemically anchored on FSs. The resultant solid bio‐catalysts exhibited very good reusability in many catalytic reactions. Getting provoked from the green chemistry aspects and benefits of FS‐based catalysts, we confer the recent literature and progress focusing on the significance of FSs in heterogeneous catalysis. This review covers the preparative methods, types and catalytic applications of FSs. A special emphasis is given to the metal‐free FS catalysts, multiple FS‐based catalysts and magnetic FSs. Through this review, we presume that the contribution of FSs to green chemistry can be well understood. The future perspective of FSs and the improvements still required for implementing FS‐based catalysts in practical applications have been narrated at the end of this review.

show abstract

“…In addition to oxidation, thiol FSs could undergo other significant chemical modifications as described here . Thiol FS has undergone a nucleophilic substitution with chloroethanol.…”

Section: Conventional Fss: Types and Their Chemical Modificationsmentioning

confidence: 99%

Section: Conventional Fss: Types and Their Chemical Modificationsmentioning

confidence: 99%

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Antony

Marimuthu

Yang

et al. 2019

The Chemical Record

View full text Add to dashboard Cite

show abstract

“…showed the use of another new catalyst containing copper nanosilica thiol‐based dendritic material, for obtaining benzimidazoles ( 8 ). The reaction between 4 and aryl aldehydes ( 7 ) took 15–80 min, when stirred in ethylacetate at 50°C and afforded 88–100% of the product (Scheme , Table , entry 3) . However, Kalhor and co‐workers performed this coupling reaction using nano‐copper Y zeolite (NCZ) as a catalyst .…”

Section: Nano‐transition Metal Catalyzed Oxidative Coupling Of O‐phenmentioning

confidence: 99%

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

Singhal

Khanna

Panda

et al. 2019

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Benzimidazole is a heterocyclic moiety of immense importance as it acts as a primary “biolinker” in diverse synthetic routes to obtain bioactive compounds. Substituted benzimidazoles are known to possess a varied range of pharmacological applications, namely, anti‐cancer, anti‐diabetic, anti‐inflammatory, and antiviral like anti‐HIV and anti‐fungal. A number of reviews covering the important aspects of benzimidazoles such as pharmacological activities, SAR studies, and well‐known methods of synthesis have appeared in the literature. However, green synthetic methods particularly using transition metal (TM) catalysts and their nanoparticles, although being more viable and extensively applied by researchers in the present scenario, have not been exclusively and expansively reviewed. Besides this, the vital precursors required for knitting the skeleton of benzimidazole are mainly o‐aryldiamines. The conventional synthesis generally involved the condensation of these diamines with carbonyl/carboxylic acid derivatives either via high temperature heating or via adding strong acids, mostly resulting in poor yields or mixtures. However, recent trends are replacing these conditions by mild and green conditions through TM catalysts. Therefore, the current review emphasizes on the recent trends adopted in the synthesis of benzimidazoles using condensation reaction of o‐phenylenediamines and various aldehydes/ester/amide/alcohols with TM in a catalytic role in nanoform and under environmentally benign green conditions.

show abstract

“…Importantly, two different approaches are being followed to construct/prepare these biaryl compounds. One is by the condensation of ophenylenediamines with alcohols, [10] aldehydes [11] or carboxylic acids, [12] and the other is by cross de-hydrogenative coupling via C-H activation of benzimidazole, [13] which requires high temperature, strong acids, expensive catalysts and long reaction time. A vast literature is available on C-H functionalizations on simple and highly active nuclei such as oxazole, [14] thiazole, [15] triazoles, [16] indole, [17] benzoxazole, [14b,18] and benzthiazole, [14b,19] while only a few exist for benzimidazole.…”

Section: Introductionmentioning

confidence: 99%

Benzimidazole bearing Pd–PEPPSI complexes catalyzed direct C2‐arylation/heteroarylation ofN‐substituted benzimidazoles

Gokanapalli

Motakatla

Peddiahgari

2020

Applied Organom Chemis

View full text Add to dashboard Cite

A convenient and highly efficient palladium‐catalyzed direct C2‐arylation/heteroarylation of N‐substituted benzimidazole derivatives such as N‐benzyl/3‐chlorobenzyl/2,4,6‐trimethylbenzyl/2,4,6‐triisopropylbenzyl/aryl benzimidazoles with various aryl/heteroaryl bromides in the presence of Pd–PEPPSI (palladium‐pyridine enhanced pre‐catalyst preparation stabilization and initiation) complexes is reported. In order to that we have prepared a series of different symmetrical and unsymmetrical N,N′‐diaralkyl benzimidazole‐bearing Pd–PEPPSI complexes. Among all of the the prepared complexes, Pd–PEPPSI‐3 effectively tuned the reaction at a relatively higher rate under mild reaction conditions in an ethanol–water system. In addition, the catalytic process avoids the use of external ligand and additives. Further the reactivity was compared with commercially available copper‐N‐heterocyclic carbene catalyst, but the reaction was less successful. With the optimized reaction conditions, a wide range of 2‐aryl/heteroaryl‐N‐substituted benzimidazoles were synthesized in good to excellent yields via Csp2‐H/Csp2‐X biaryl cross‐coupling.

show abstract

Copper containing nanosilica thioalated dendritic material: A recyclable catalyst for synthesis of benzimidazoles and benzothiazoles

Cited by 24 publications

References 76 publications

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Functionalized Silicas for Metal‐Free and Metal‐Based Catalytic Applications: A Review in Perspective of Green Chemistry

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

Benzimidazole bearing Pd–PEPPSI complexes catalyzed direct C2‐arylation/heteroarylation ofN‐substituted benzimidazoles

Contact Info

Product

Resources

About