K2S2O8 promoted metal-free direct C-alkylation of acetophenones with alcohols DOI

Deepak Gautam,

Puneet Singh Gahlaut,

Shristi Pathak

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(48), P. 9519 - 9523

Published: Jan. 1, 2023

A metal-free synthetic methodology for the C-alkylation of acetophenones following a hydrogen borrowing-like pathway using commercially available inorganic oxidant K 2 S O 8 in conjunction with KO t Bu is reported.

Language: Английский

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
Unravelling a bench-stable zinc-amide compound as highly active multitasking catalyst for radical-mediated selective alk(en)ylation of unactivated carbocycles under mild conditions DOI Creative Commons

Sangita Sahoo,

Subarna Manna,

Arnab Rit

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(14), P. 5238 - 5247

Published: Jan. 1, 2024

The direct functionalization of unactivated organic moieties

Language: Английский

Citations

6
Oxygen-Dependent Ligand-Controlled Iron-Catalyzed Chemoselective Synthesis of Olefins and Vinyl Nitriles DOI
Amit Kumar Guin, Subhajit Chakraborty,

Subhankar Khanra

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(13), P. 2540 - 2545

Published: March 28, 2024

An oxygen-dependent ligand-controlled chemoselective synthesis of vinyl nitriles and E-olefins by coupling a variety alcohols benzyl cyanides, catalyzed well-characterized, air-stable, easy-to-prepare Fe(II) catalyst (1a) bearing redox-active arylazo pincer (L1a) is reported. The azo-moiety the ligand backbone acts as an electron hydrogen reservoir, enabling 1a to efficiently produce broad spectrum in moderate good yields selectively under oxygen argon atmosphere, respectively.

Language: Английский

Citations

6
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
Nickel‐Catalyzed Sequential Dehydrogenation and Cyclization of 2‐Amino(Nitro)‐benzyl Alcohols with Alkyl Alcohols: Synthesis of C‐3‐Substituted Quinolines DOI

Motahar Sk,

Atanu Bera, Debasis Banerjee

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 15(11)

Published: April 26, 2023

Abstract We herein reported a general and efficient Ni‐catalyzed protocol for sequential double de‐hydrogenative cyclization of 2‐amino(nitro)‐benzyl alcohols with primary to C‐3‐substituted quinolines releasing water dihydrogen as by products. As special highlight, late stage functionalization cholesterol derivative including chemo‐selective transformations citronellol, fatty acid derived oleyl alcohol long chain C 4 −C 14 alkyl were reported. Initial mechanistic studies deuterium‐labelling experiments perform establish the cyclization.

Language: Английский

Citations

11
LiOtBu-promoted synthesis of bis(3-indolyl)methanes by the alkylation of indoles with alcohols under air DOI Creative Commons
Nguyen Hai Yen,

Thu Hue Tran,

Ha Nam

et al.

RSC Advances, Journal Year: 2024, Volume and Issue: 14(4), P. 2341 - 2345

Published: Jan. 1, 2024

Bis(3-indolyl)methanes (BIMs) are known for their important bioactivities, which include anti-cancer, anti-inflammatory, antibacterial, and antioxidant properties. In this study, we disclosing a metal catalyst-free synthesis of BIMs in high yields via the alkylation reaction indoles alcohols presence lithium tert-butoxide base. Notably, oxygen air played an role as oxidant facilitation transformation. Interestingly, unactivated aliphatic could be successfully used alkylating reagents reactions indole. Especially, several chemical intermediates detected by GC-MS gave information about mechanism insights. This method demonstrated cost environmental advantages development green processes.

Language: Английский

Citations

3
Potent pincer-zinc catalyzed homogeneous α-alkylation and Friedländer quinoline synthesis reaction of secondary alcohols/ketones with primary alcohols DOI
Debashis Jana, Sima Roy,

Srijita Naskar

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6393 - 6408

Published: Jan. 1, 2024

Herein, we describe an air- and moisture-stable, homogeneous zinc catalyst stabilised using electron deficient N^N^N pincer-type ligand.

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
α-Alkylation of ketones with primary alcohols by an active non-noble metal Cu/CuOx catalyst DOI

Dongyuan Yang,

Hongli Wang, Chun‐Ran Chang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(5), P. 970 - 975

Published: Dec. 23, 2023

Development of convenient and effective heterogeneous non-noble metal catalysts for α-alkylation ketones with alcohols is challenging in catalysis. Here, we report active Cu/CuOx the construction C-C bonds by through borrowing hydrogen methodology. The optimal Cu/CuOx-250 catalyst exhibits good catalytic performance reactions to give corresponding products 50-96% yields. are characterized different analysis techniques such as XRD, TEM, XPS, H

Language: Английский

Citations

3
Fabricating Effective and Recyclable Cadmium‐based Coordination Polymer for Selective Synthesis of 1,5‐Benzodiazepines DOI
Li Chen, Jiahao Li, Likui Wang

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(12)

Published: Oct. 9, 2023

Abstract Metal coordination polymers are widely applied in the synthesis of heterocyclic compounds due to advantages highly dispersed metal active sites, low cost and strong designability. Herein, employing 9‐benzyl‐3,6‐di( 1H ‐pyrazol‐1‐yl)‐ 9H ‐carbazole (BPC) as a ligand, cadmium‐coordinated polymer compound (Cd‐BPC) was facilely prepared by solvothermal method characterized energy dispersive spectrometer (EDS), flourier‐transform infrared spectroscopy (FT‐IR), scanning electron microscope (SEM), transmission microscopy (TEM) X‐ray photoelectron spectrometry (XPS). Employing Cd‐BPC catalyst, 1,5‐benzodiazepine derivatives were produced with relatively high yields through reaction o ‐phenylenediamine ketones, alcohols. Additionally, could be reused for at least 5 times without significant decrease.

Language: Английский

Citations

2