Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C═C Bond Cleavage DOI
Yi Peng,

Yan-Hui Fan,

Si‐Yuan Li

et al.

Organic Letters, Journal Year: 2019, Volume and Issue: 21(20), P. 8389 - 8394

Published: Oct. 7, 2019

C═C bond breaking to access the C═N remains an underdeveloped area. A new protocol for cleavage of alkenes under nonoxidative conditions produce imines via iron-catalyzed nitrene transfer reaction 4-hydroxystilbenes with aryl azides is reported. The success various sequential one-pot reactions reveals that good compatibility this method makes it very attractive synthetic applications. On basis experimental observations, a plausible mechanism also proposed.

Language: Английский

Manganese-catalyzed hydrogenation, dehydrogenation, and hydroelementation reactions DOI
Kuhali Das, Satyadeep Waiba, Akash Jana

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(11), P. 4386 - 4464

Published: Jan. 1, 2022

The emerging field of organometallic catalysis has shifted towards research on Earth-abundant transition metals due to their ready availability, economic advantage, and novel properties. In this case, manganese, the third most abundant transition-metal in Earth's crust, emerged as one leading competitors. Accordingly, a large number molecularly-defined Mn-complexes been synthesized employed for hydrogenation, dehydrogenation, hydroelementation reactions. regard, catalyst design is based three pillars, namely, metal-ligand bifunctionality, ligand hemilability, redox activity. Indeed, developed catalysts not only differ chelating atoms they possess but also working principles, thereby different turnover numbers product molecules. Hence, critical assessment molecularly defined manganese terms atoms, reaction conditions, mechanistic pathway, significant. Herein, we analyze complexes catalytic activity, versatility allow multiple transformations routes convert substrates target This article will be helpful get significant insight into design, aiding design.

Language: Английский

Citations

160

Transition metals-catalyzed amination of biomass feedstocks for sustainable construction of N-heterocycles DOI
Qiong Yan, Xu Wu, Hao Jiang

et al.

Coordination Chemistry Reviews, Journal Year: 2023, Volume and Issue: 502, P. 215622 - 215622

Published: Dec. 26, 2023

Language: Английский

Citations

79

Manganese Catalyzed Acceptorless Dehydrogenative Coupling Reactions DOI
Satyadeep Waiba, Biplab Maji

ChemCatChem, Journal Year: 2019, Volume and Issue: 12(7), P. 1891 - 1902

Published: Dec. 21, 2019

Abstract Acceptorless dehydrogenative coupling (ADC) has emerged as a powerful tool in the chemists’ arsenal for construction of various carbon‐carbon and carbon‐heteroatom bonds. These protocols are highly atom economical environmentally benign they do not require pre‐functionalized starting material produce only dihydrogen (and water) by‐product. This technique, coupled with Earths’ abundant less toxic manganese catalysis, can prove to be vital strategy generation molecular complexity from simple materials. Manganese catalyzed DHC been growing interest, low‐ high‐valent catalysts have developed. were demonstrated show excellent catalytic activity formation carbon‐carbon, bonds, cascade reactions. In this mini‐review, we would like highlight recent progress that made ADC

Language: Английский

Citations

95

Homogeneous Nickel-Catalyzed Sustainable Synthesis of Quinoline and Quinoxaline under Aerobic Conditions DOI

Amreen K. Bains,

Vikramjeet Singh, Debashis Adhikari

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(23), P. 14971 - 14979

Published: Nov. 11, 2020

Dehydrogenative coupling-based reactions have emerged as an efficient route toward the synthesis of a plethora heterocyclic rings. Herein, we report efficacious, nickel-catalyzed two important heterocycles such quinoline and quinoxaline. The catalyst is molecularly defined, phosphine-free, can operate at mild reaction temperature 80 °C. Both be easily assembled via double dehydrogenative coupling, starting from 2-aminobenzyl alcohol/1-phenylethanol diamine/diol, respectively, in shorter span time. This environmentally benign synthetic protocol employing inexpensive rival many other transition-metal systems that been developed for fabrication putative heterocycles. Mechanistically, dehydrogenation secondary alcohol follows clean pseudo-first-order kinetics exhibits sizable kinetic isotope effect. Intriguingly, this provides example storing trapped hydrogen ligand backbone, avoiding metal-hydride formation. Easy regeneration oxidized form under aerobic/O2 oxidation makes eco-friendly easy to handle.

Language: Английский

Citations

79

Advancements in multifunctional manganese complexes for catalytic hydrogen transfer reactions DOI
Kuhali Das, Milan Kr. Barman, Biplab Maji

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(69), P. 8534 - 8549

Published: Jan. 1, 2021

Manganese catalyzed hydrogen transfer reactions enabled net reductions and cascade CC- CN-bond formation reactions. The success is aided by multifunctional ligand design namely metal–ligand bifunctionality, hemilability, redox non-innocence.

Language: Английский

Citations

61

Manganese‐Catalysed Dehydrogenative Coupling – An Overview DOI
K. Rohit,

Sankaran Radhika,

Salim Saranya

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(8), P. 1602 - 1650

Published: Jan. 29, 2020

Abstract Manganese‐catalysed reactions have attracted great attention recently due to the high relative abundance and cheap eco‐friendly behaviour. Applications of manganese catalysis in cross‐dehydrogenative coupling are among hottest areas since 90% contributions very recent. Dehydrogenation alcohols using Mn‐pincer systems is highly explored nowadays for cross‐coupling synthesise a variety products Mn‐catalysed C−H activation, radical applied dehydrogenative couplings various synthons. This review focuses on synthesis synthetically as well biologically important motifs such carbonyl compounds, olefins, nitrogen heterocycles, amines, imines, etc. manganese‐catalysed reactions. magnified image

Language: Английский

Citations

69

Recent Progress in the Synthesis of Heterocycles through Base Metal‐Catalyzed Acceptorless Dehydrogenative and Borrowing Hydrogen Approach DOI
Avijit Mondal, Rahul Sharma,

Debjyoti Pal

et al.

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(26), P. 3690 - 3720

Published: June 15, 2021

Abstract Development in the area of acceptorless dehydrogenation (AD) and borrowing hydrogen (BH) catalysis emerge as one potential tools for various C−C C‐heteroatom bond forming reactions. Alcohols, which are important lignocellulosic biomass products, act pivotal electrophilic coupling partners such processes interestingly only H 2 or O is eliminated a byproduct. Initially, was developed by use noble metal catalysts. Recently, base metals Mn, Fe, Co, Ni proved to be environmentally benign inexpensive alternatives application AD BH methods. This transition catalyzed approaches also allow access toward plethora structurally heterocyclic molecules via atom economical strategy. Herein, we summarize current rising expansion heterocycles synthesis through hydrogenation

Language: Английский

Citations

56

Borrowing Hydrogen and Acceptorless Dehydrogenative Coupling in the Multicomponent Synthesis of N‐Heterocycles: A Comparison between Base and Noble Metal Catalysis DOI Creative Commons

Natalie Hofmann,

Kai C. Hultzsch

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(46), P. 6206 - 6223

Published: Nov. 4, 2021

Abstract Acceptorless dehydrogenative coupling reactions (ADC) and hydrogen transfer strategies (HT) provide a powerful tool in the multicomponent formation of N ‐ heterocycles. A broad variety complex products can be obtained starting from simple, cheap commercially available reagents. The protocols are highly atom‐efficient, as water, dihydrogen, or some cases peroxide, only by‐products. Moreover, neither further reducing oxidizing agents, nor external general required. Especially base metal‐catalyzed become ever more important. Therefore, recent years, various different manganese, iron, cobalt, nickel copper catalysts have been developed. This Minireview highlights progress that has made by using abundant metal complexes to promote cyclizations for heterocycles compares their performance with noble catalyst systems.

Language: Английский

Citations

52

Cobalt Nanoparticles catalyzed N‐Heterocycles Synthesis via Acceptorless Dehydrogenative Coupling DOI

Changyue Ren,

Shuiyan Chen,

Zeli Yuan

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: unknown

Published: July 29, 2024

Abstract The acceptorless dehydrogenation reaction is a sustainable and atom‐economical methodology in organic synthesis, resulting the byproducts of only hydrogen or water. Herein, robust Co−Si/CN catalyst (derived from ZIF@SiO 2 composite) has been synthesized through one‐step assembly process via pyrolysis etching. This employed for dehydrogenative coupling 2‐aminoalcohols with secondary alcohols, enabling efficient conversion various substrates into desired quinoline pyridine derivatives yield up to 94 %.

Language: Английский

Citations

8

Continuous solvent-free synthesis of imines over uip-γ-Al2O3-CeO2 catalyst in a fixed bed reactor DOI

Xiao Cao,

Jiaheng Qin,

Galian Gou

et al.

Applied Catalysis B Environment and Energy, Journal Year: 2020, Volume and Issue: 272, P. 118958 - 118958

Published: April 15, 2020

Language: Английский

Citations

44