Exploring Thermomyces lanuginosus Lipase (TLL)‐PdNPs Nanohybrid as Suitable Catalyst for One‐pot Synthesis of Bis(3‐indolyl)phenylmethane DOI Creative Commons
A. Sofia Santos, Noelia Losada‐Garcia, Carla Garcia‐Sanz

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 16(3)

Published: Nov. 27, 2023

Abstract Palladium nanohybrids were synthesized and applied to the one‐pot synthesis of bis(3‐indolyl)methanes by selective C−C bond reaction from benzyl alcohol indole. A T. lanuginosus lipase‐palladium nanoparticles hybrid (Pd@TLL) was synthesized, yielding PdNPs with an average diameter size 5 nm. This heterogeneous catalyst first tested in oxidation benzaldehyde different solvents. Then, direct formation bis(3‐indolyl)methane, situ coupling, successfully evaluated under conditions, obtaining >99 % conversion at 80 °C toluene, a TOF value 9 min −1 89 pure water , demonstrating versatility these biohybrids.

Language: Английский

Harnessing alcohols as sustainable reagents for late-stage functionalisation: synthesis of drugs and bio-inspired compounds DOI
Sourajit Bera, Lalit Mohan Kabadwal, Debasis Banerjee

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(9), P. 4607 - 4647

Published: Jan. 1, 2024

This review collectively discussed the utilisation of alcohols in various organic transformations and their application toward intermediates drugs, drug derivatives natural product-like molecules.

Language: Английский

Citations

16

Unlocking Diversity: From Simple to Cutting-Edge Synthetic Methodologies of Bis(indolyl)methanes DOI
Pankaj Teli, Shivani Soni, Sunita Teli

et al.

Topics in Current Chemistry, Journal Year: 2024, Volume and Issue: 382(1)

Published: Feb. 25, 2024

Language: Английский

Citations

12

Alcohol Dehydrogenation-Triggered Selective C3-Alkylation of Indoles by Homogeneous Azo-aromatic Cobalt Catalysts DOI

kamal kamal,

Manas Khatua, Swati Rani

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5827 - 5843

Published: April 10, 2023

Herein, we report azo-benzimidazole containing cobalt complexes (1-3) for alcohol dehydrogenation-triggered C3-alkylation of indoles. In 1-3, ligands are redox noninnocent and showed facile irreversible L/L• reduction followed by Co(II)/Co(I) in close-lying potentials. Taking advantage events the first aerial dehydrogenation alcohols to their corresponding carbonyl compounds is explored. Subsequently, indole was studied using as alkylating agents. The developed catalytic protocol found be efficient very selective. It has a broad substrate scope good functional group tolerance. As far aware, it homogeneous catalyst agent. Detailed mechanistic studies, including deuterium labeling experiment, have suggested borrowing hydrogen method indole. coordinated ligand, cooperatively with couple, oxidized alkoxide radical pathway result compound (Scheme 1), which on subsequent condensation generates alkylideneindolenine intermediate "X". Reduction "X" an azo-anion Co(I) resulted C3-alkylated

Language: Английский

Citations

22

N-Alkylation of Amines by C1–C10 Aliphatic Alcohols Using A Well-Defined Ru(II)-Catalyst. A Metal–Ligand Cooperative Approach DOI
Amit Kumar Guin, Subhasree Pal, Subhajit Chakraborty

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(9), P. 5944 - 5961

Published: April 13, 2023

A Ru(II)-catalyzed efficient and selective N-alkylation of amines by C1-C10 aliphatic alcohols is reported. The catalyst [Ru(L1a)(PPh3)Cl2] (1a) bearing a tridentate redox-active azo-aromatic pincer, 2-((4-chlorophenyl)diazenyl)-1,10-phenanthroline (L1a) air-stable, easy to prepare, showed wide functional group tolerance requiring only 1.0 mol % (for N-methylation N-ethylation) 0.1 loading for with C3-C10 alcohols. array N-methylated, N-ethylated, N-alkylated were prepared in moderate good yields via direct coupling 1a efficiently catalyzes the diamines selectively. It even suitable synthesizing using (aliphatic) diols producing tumor-active drug molecule MSX-122 yield. excellent chemo-selectivity during oleyl alcohol monoterpenoid β-citronellol. Control experiments mechanistic investigations revealed that 1a-catalyzed reactions proceed borrowing hydrogen transfer pathway where removed from dehydrogenation step stored ligand backbone 1a, which subsequent steps transferred situ formed imine intermediate produce amines.

Language: Английский

Citations

22

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

A strategic approach for Csp3–H functionalization of 9H-fluorene: an acceptorless dehydrogenation and borrowing hydrogen approach DOI
Rahul Sharma, Avijit Mondal,

Arup Samanta

et al.

Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(3), P. 611 - 617

Published: Jan. 1, 2023

Herein, we described the selective synthesis of both alkylated and alkenylated fluorenes using a single SNS ligand derived nickel complex.

Language: Английский

Citations

13

Multi-hydroxyl POSS supported iridium complexes as a recyclable catalyst for selective synthesis of N-/C-substituted indoles and the total synthesis of HIV-1 fusion inhibitor DOI
Jiahao Li, Li Chen, Likui Wang

et al.

Journal of Catalysis, Journal Year: 2023, Volume and Issue: 429, P. 115205 - 115205

Published: Nov. 24, 2023

Language: Английский

Citations

12

HFIP-mediated C-3-alkylation of indoles and synthesis of indolo[2,3-b]quinolines & related natural products DOI

Auqib Rashid,

Waseem I. Lone,

Preeti Dogra

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(17), P. 3502 - 3509

Published: Jan. 1, 2024

An expeditious metal free C-3 alkylation of indoles and its NIS-mediated deviation to indolo[2,3- b ]quinolines is reported. Applications these strategies in accessing bioactive natural products have also been demonstrated.

Language: Английский

Citations

5

Synthesis of Bis(3‐indolyl)methanes Mediated by Potassium tert‐Butoxide DOI Creative Commons
A. Sofia Santos,

Rita Ferro,

Nuno Viduedo

et al.

ChemistryOpen, Journal Year: 2023, Volume and Issue: 12(1)

Published: Jan. 1, 2023

The indole moiety is an important N-heterocycle found in natural products, and a key structural component of many value-added chemicals including pharmaceuticals. In particular, bis(3-indolyl)methanes (BIMs) are subgroup indoles, composed two units. Herein, we report the development simple method to access BIMs derivatives yields up 77 % by exploiting tBuOK-mediated coupling reaction indoles benzyl alcohols.

Language: Английский

Citations

10

Orthometallated Pd(ii) C^N^S pincer complex catalyzed sustainable synthesis of bis(indolyl)methanesviaacceptorless dehydrogenative coupling of alcohols DOI
Savarimuthu Selvan Clinton, Rengan Ramesh, J.G. Małecki

et al.

Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(11), P. 3358 - 3365

Published: Jan. 1, 2023

New orthometallated Pd( ii ) C^N^S pincer catalyst-mediated sustainable and cost-effective synthesis of pharmacologically important bis(indolyl)methanes (23 examples up to 95% yield) via ADC is reported.

Language: Английский

Citations

10