Supported Nickel Nanoparticles as Catalyst in Direct sp3 C–H Alkylation of 9H‐Fluorene Using Alcohols as Alkylating Agent DOI Creative Commons
Raju Dey,

M. Vageesh,

Harsh Joshi

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 14, 2024

Abstract Herein, we report an inexpensive first‐row transition metal Ni heterogeneous catalytic system for the C sp 3 ‐mono alkylation of fluorene using alcohols as alkylating agents via borrowing hydrogen strategy. The protocol displayed versatility with high yields desired products various types primary alcohols, including aryl/hetero aryl methanols, and aliphatic agents. catalyst NPs@N−C was synthesized high‐temperature pyrolysis strategy, ZIF‐8 sacrificial template. characterized by XPS, HR‐TEM, HAADF‐STEM, XRD ICP‐MS. is stable even in air at room temperature, excellent activity could be recycled 5 times without appreciable loss its activity.

Language: Английский

Design, synthesis, structure elucidation, antimicrobial, molecular docking, and SAR studies of novel urea derivatives bearing tricyclic aromatic hydrocarbon rings DOI
Farid M. Sroor,

Ahmed F. El‐Sayed,

Mohamed Abdelraof

et al.

Archiv der Pharmazie, Journal Year: 2024, Volume and Issue: 357(6)

Published: March 11, 2024

Abstract The targeted compounds were prepared using both (9 H ‐fluoren‐9‐ylidene)hydrazine ( 1 ) and 10 ‐phenothiazine 2 as starting materials. treatment of or with different isocyanates afforded the title 7a–d , 8a 8b in excellent yield. All characterized ascertained by infrared, nuclear magnetic resonance, elemental analyses well single‐crystal X‐ray diffraction. antimicrobial efficiency all was tested vitro, a noticeable inhibition activity against Bacillus subtilis Staphylococcus aureus Pseudomonas aeruginosa Klebsiella pneumoniae Candida albicans obtained 7a 7b . Moreover, biofilm mechanism strongly inhibited for bacterial pathogens, percentage ratio more than 55%. findings from molecular docking simulation revealed that exhibited favorable binding energies interacted effectively active sites sterol 14‐demethylase, dihydropteroate synthase, gyrase B, LasR (major transcriptional activator P. ), carbapenemase C. S. B. subtills K. respectively. These results suggest have potential to inhibit these enzymes demonstrate promising properties. silico evaluation drug likeness absorption, distribution, metabolism, excretion, toxicity (ADMET) profiles demonstrated their compatibility Lipinski's, Ghose's, Veber's, Muegge's, Egan's rules. possess physicochemical properties, making them candidates continued development efforts.

Language: Английский

Citations

18
Noninnocent Azo-Aromatic Cobalt(II)-Catalyzed sp3 C–H Alkylation of Fluorenes with Alcohols DOI

kamal kamal,

Subhas Samanta

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1910 - 1926

Published: Jan. 11, 2024

Herein, employing well-defined redox noninnocent cobalt(II) complexes an efficient sp3 C–H alkylation of fluorenes using alcohols as alkylating agents to result in alkylated is reported. The catalytic protocol was versatile with various and benzyl alcohols. It also showed very good functional group tolerance both fluorenes. Moreover, single-step simultaneous di C–C well the C–N reaction observed this protocol. Such selective dialkylation indeed beneficial. Several control experiments, deuterium labeling, 1H NMR kinetic studies have revealed a ligand radical-based borrowing hydrogen mechanism involving azo-aromatic cobalt catalysts for

Language: Английский

Citations

9
Zn(II)‐Stabilized Azo‐Anion Radical Catalyzed Sustainable C−C Bond Formation: Regioselective Alkylation of Fluorene, Oxindole, and Indoles DOI
Subhasree Pal, Amit Kumar Guin, Subhajit Chakraborty

et al.

ChemCatChem, Journal Year: 2024, Volume and Issue: 16(10)

Published: Feb. 7, 2024

Abstract Herein we report a sustainable approach for the alkylation of ketones, 9 H ‐fluorene, oxindole, and indole using alcohols as alkylating agent catalyzed by well‐defined air‐stable zinc catalyst ( 1 ) tridentate redox non‐innocent arylazo ligand, 2‐((4‐chlorophenyl)diazenyl)‐1,10‐phenanthroline L ). 2–3 mol % efficiently produces substituted α‐alkylated 9‐alkylated fluorenes, C3 ‐alkylated oxindoles, indoles in moderate to good isolated yields. In aerial condition, formation bis(indolyl)methane (BIMs) derivatives were observed when subjected primary alcohols. A few drug molecules containing BIMs prepared The exhibited chemoselectivity during functionalization fluorene with oleyl alcohol β‐citronellol. control experiments, including deuterium labeling performed unveil reaction mechanism indicate that one‐electron reduced azo‐anion radical species [ ]‐formed situ, acts active catalyst. All events occur at redox‐active aryl‐azo which reservoir hydrogen electrons throughout catalytic cycle, keeping Zn(II)‐center template.

Language: Английский

Citations

9
Olefins from alcohols via catalytic acceptorless dehydrogenation coupling reactions DOI Creative Commons

Triptesh Kumar Roy,

Reshma Babu,

Ganesan Sivakumar

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(8), P. 2064 - 2089

Published: Jan. 1, 2024

Recent advances in efficient catalytic routes to olefins from alcohols (A2O) are highlighted.

Language: Английский

Citations

7
Ruthenium Complexes with NNN-Pincer Ligands for N-Methylation of Amines Using Methanol DOI

Mengxuan Bai,

Shengxin Zhang,

Zhengguo Lin

et al.

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(25), P. 11821 - 11831

Published: June 7, 2024

A series of ruthenium complexes (Ru1–Ru4) bearing new NNN-pincer ligands were synthesized in 58–78% yields. All the are air and moisture stable characterized by IR, NMR, high-resolution mass spectra (HRMS). In addition, structures Ru1–Ru3 confirmed X-ray crystallographic analysis. These Ru(II) exhibited high catalytic efficiency broad functional group tolerance N-methylation reaction amines using CH3OH as both C1 source solvent. Experimental results indicated that electronic effect substituents on considerably affects reactivity which Ru3 an electron-donating OMe showed highest activity. Deuterium labeling control experiments suggested dehydrogenation methanol to generate hydride species was rate-determining step reaction. Furthermore, this protocol also provided a ready approach versatile trideuterated N-methylamines under mild conditions CD3OD deuterated methylating agent.

Language: Английский

Citations

5
(E)‐Selective Olefination by a Cofactor‐Inspired Quinone Catalysis DOI

Shyamali Maji,

Monojit Roy,

Debashis Adhikari

et al.

ChemCatChem, Journal Year: 2025, Volume and Issue: unknown

Published: May 21, 2025

Abstract In this study, we report a photothermal method that prepares ( E )‐olefins from methyl‐substituted heteroarenes under very mild reaction conditions. The photocatalyst is pyrene dione (PD) molecule has significant absorbance in the visible light spectrum and can afford persistent semiquinonate radical owing to π‐delocalized backbone. This conducts hydrogen atom transfer reactions facilitate dehydrogenation of large number alcohols. Leveraging on dehydrogenating ability PD easily 2e − /2H + redox shuttles, olefination was conducted heteroarene methyl, fluorenes Furthermore, catalytic process works aerobic conditions since oxygen regenerates catalyst. methodological development improvement over many transition metal catalysts for task, which often work at high temperature anaerobic

Language: Английский

Citations

0
Pincer Nickel‐Catalyzed Olefination of Alcohols with Benzylphosphine Oxides DOI

Yu‐Tong Duan,

Bo Yang, Zhong‐Xia Wang

et al.

Chemistry - An Asian Journal, Journal Year: 2024, Volume and Issue: 19(11)

Published: April 11, 2024

Abstract N,N,P‐Pincer nickel complexes effectively catalyze reaction of alcohols with benzylphosphine oxides to form alkenes in good yields. The protocol suits for a wide scope substrates and generates only E ‐configurated alkenes. method also shows compatibility functional groups. Methoxy, methylthio, trifluoromethyl, ketal, fluoro, chloro, bromo, thienyl, furyl groups are tolerated. mechanism studies support that the proceeds through catalytic dehydrogenation aldehydes or ketones followed by condensation benzyldiphenylphosphine presence KO t Bu.

Language: Английский

Citations

1
Synthesis of 2,7-Diaryl Substituted Fluorenes and Fluorenones DOI Open Access
Yong‐Qing Li, Yuqing Peng,

Yucai Cao

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(5), P. 1494 - 1494

Published: Jan. 1, 2024

2,7-Diaryl substituted fluorenes and fluorenones are widely used in fields of organic semiconductor, chemosensor, metallocene catalysis.Traditional synthesis methods can not meet the requirements flexible molecular structures regulation diverse properties.Aryl-aryl cross coupling reactions based on catalysis Pd Ni complexes have become efficient for preparation 2,7-diaryl fluorenones.Various types metal catalysts with phosphine ligands N-heterocyclic carbene been applied.The synthetic or without 9-substitutions, conditions application reviewed.The challenges various at present summarized a brief outlook possible solutions is provided.

Language: Английский

Citations

1
Copper-Catalyzed C(sp3)–H Alkylation of Fluorene with Primary and Secondary Alcohols using Borrowing Hydrogen Method DOI
Ratnakar Saha, Suraj Kumar Maharana, Narayan Ch. Jana

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(74), P. 10144 - 10147

Published: Jan. 1, 2024

Despite the limited success of copper-catalyzed alkylations, (NNS)CuCl proved to be an effective catalyst for sp

Language: Английский

Citations

1
Iron-Catalyzed sp3 C–H Alkylation of Fluorene with Primary and Secondary Alcohols: A Borrowing Hydrogen Approach DOI
Ratnakar Saha,

Bhairab Chand Hembram,

Surajit Panda

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16223 - 16241

Published: Aug. 23, 2024

The utilization of earth-abundant, cheap, and nontoxic transition metals in important catalytic transformations is essential for sustainable development, iron has gained significant attention as the most abundant metal. A mixture FeCl2 (3 mol %), phenanthroline (6 KOtBu (0.4 eqivalent) was used an effective catalyst sp3 C–H alkylation fluorene using alcohol a nonhazardous alkylating partner, eco-friendly water formed only byproduct. substrate scope includes wide range substituted fluorenes benzyl alcohols. reaction equally with challenging secondary alcohols unactivated aliphatic Selective mono-C9-alkylation yielded corresponding products good isolated yields. Various postfunctionalizations C-9 alkylated were performed to establish practical utility this alkylation. Control experiments suggested homogeneous path involving borrowing hydrogen mechanism formation subsequent reduction 9-alkylidene intermediate.

Language: Английский

Citations

1