Waste-Minimized Continuous-Flow Synthesis of Oxindoles Exploiting a Polymer-Supported N Heterocyclic Palladium Carbene Complex in a CPME/Water Azeotrope DOI Creative Commons
Nihad Salameh, Francesco Ferlin, Federica Valentini

et al.

ACS Sustainable Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 10(11), P. 3766 - 3776

Published: March 10, 2022

Herein, we report the development of an effective synthetic protocol for synthesis oxindoles in flow based on a C(sp3)–H activation process promoted by supported N-heterocyclic carbene palladium heterogeneous catalytic system using cyclopentyl methyl ether (CPME) as reaction medium. The design catalyst, selection solvent medium, and definition tailored continuous reactor have been all designed to establish efficient waste-minimized intramolecular cyclization N-methyl-2-halo-acetanilides. use CPME its aqueous azeotropic mixture has allowed us reach high yields products with simplified precipitation workup that includes downstream separation recycling solvent. An assessment environmental safety hazard features also made order better clarify implications terms sustainability newly developed process.

Language: Английский

Privileged chiral N-heterocyclic carbene ligands for asymmetric transition-metal catalysis DOI
Daniel Janssen‐Müller, Christoph Schlepphorst, Frank Glorius

et al.

Chemical Society Reviews, Journal Year: 2017, Volume and Issue: 46(16), P. 4845 - 4854

Published: Jan. 1, 2017

An overview on the most successful chiral N-heterocyclic carbene ligands in asymmetric catalysis is given.

Language: Английский

Citations

387

N-Heterocyclic Carbene Complexes of Copper, Nickel, and Cobalt DOI
Andreas A. Danopoulos, Thomas Simler, Pierre Braunstein

et al.

Chemical Reviews, Journal Year: 2019, Volume and Issue: 119(6), P. 3730 - 3961

Published: March 7, 2019

The emergence of N-heterocyclic carbenes as ligands across the Periodic Table had an impact on various aspects coordination, organometallic, and catalytic chemistry 3d metals, including Cu, Ni, Co, both from fundamental viewpoint but also in applications, catalysis, photophysics, bioorganometallic chemistry, materials, etc. In this review, emergence, development, state art these three areas are described detail.

Language: Английский

Citations

384

Preparation and Post-Assembly Modification of Metallosupramolecular Assemblies from Poly(N-Heterocyclic Carbene) Ligands DOI

Ming‐Ming Gan,

Jiquan Liu,

Le Zhang

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 118(19), P. 9587 - 9641

Published: July 5, 2018

Although the coordination chemistry of N-heterocyclic carbenes (NHCs) with transition metals has been explored for half a century, only in past ten years metallosupramolecular assemblies based on poly-NHC ligands studied more extensively. Remarkable discrete featuring including two-dimensional metallacycles and three-dimensional metallaprisms/cages have since emerged. These are mostly obtained starting from various imidazolium or benzimidazolium salts. Driven by increasing interest new supramolecular architectures carbon donor ligands, design, construction metal become rapidly growing area research. The metal–carbene bond length is fixed to approximately 2.0 Å linear NHC–M–NHC complexes. This allows use such complexes bearing olefin-substituted NHC as templates subsequent photochemical [2 + 2] cycloaddition reactions. postassembly modification actively recent years. In this review, we focus synthetic methods, characterization, structural features, modifications ligands.

Language: Английский

Citations

291

Pushing Electrons—Which Carbene Ligand for Which Application? DOI
Dominik Munz

Organometallics, Journal Year: 2018, Volume and Issue: 37(3), P. 275 - 289

Published: Feb. 12, 2018

This tutorial explores the diversity and characteristics of C-donor ligands. Particular emphasis is put on conceptual design electronic properties for applications in coordination chemistry. More specifically, implications both σ π effects are discussed. Cyclic (alkyl)(amino)carbenes as well methanediides carbones brought perspective to "conventional" N-heterocylic carbenes, mesoionic Fischer Schrock carbene

Language: Английский

Citations

228

Reusable N-Heterocyclic Carbene Complex Catalysts and Beyond: A Perspective on Recycling Strategies DOI
Wenlong Wang, Lifeng Cui, Peng Sun

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 118(19), P. 9843 - 9929

Published: May 31, 2018

With the continuous development of N-heterocyclic carbene (NHC) chemistry during past decade, NHC metal complexes have gained wide applications in research field organometallic catalysis. The recycling and reuse complexes, which undergone expansion diversification, can enhance their catalytic performance, extend range application, afford new routes to green chemistry. Taking complex catalysts as main topic, this review intends present a comprehensive study strategies catalysts. By an elaborative summarization classification strategies, clear picture all available for is presented advantages disadvantages various specific reactions are discussed detail. This written with hope serving modest spur induce other scientists' further contributions fields catalyst sustainable

Language: Английский

Citations

202

High-Oxidation-State 3d Metal (Ti–Cu) Complexes withN-Heterocyclic Carbene Ligation DOI
Jun Cheng, Lijun Wang, Peng Wang

et al.

Chemical Reviews, Journal Year: 2018, Volume and Issue: 118(19), P. 9930 - 9987

Published: July 16, 2018

High-oxidation-state 3d metal species have found a wide range of applications in modern synthetic chemistry and materials science. They are also implicated as key reactive biological reactions. These thus prompted explorations their formation, structure, properties. While the traditional wisdom regarding these was gained mainly from complexes supported by nitrogen- oxygen-donor ligands, recent studies with N-heterocyclic carbenes (NHCs), which widely used for preparation low-oxidation-state transition organometallic chemistry, led to large variety isolable high-oxidation-state NHC ligation. Since first report this area 1990s, type been reported titanium(IV), vanadium(IV,V), chromium(IV,V), manganese(IV,V), iron(III,IV,V), cobalt(III,IV,V), nickel(IV), copper(II). With aim providing an overview intriguing field, Review summarizes our current understanding methods, structure spectroscopic features, reactivity, catalytic titanium copper. In addition progress, factors affecting stability reactivity presented, well perspectives on future efforts.

Language: Английский

Citations

159

Recent advances in phosphorescent platinum complexes for organic light-emitting diodes DOI Creative Commons
Cristina Cebrián, Matteo Mauro

Beilstein Journal of Organic Chemistry, Journal Year: 2018, Volume and Issue: 14, P. 1459 - 1481

Published: June 18, 2018

Phosphorescent organometallic compounds based on heavy transition metal complexes (TMCs) are an appealing research topic of enormous current interest. Amongst all different fields in which they found valuable application, development emitting materials TMCs have become crucial for electroluminescent devices such as phosphorescent organic light-emitting diodes (PhOLEDs) and electrochemical cells (LEECs). This interest is driven by the fact that luminescent with long-lived excited state lifetimes able to efficiently harvest both singlet triplet electro-generated excitons, thus opening possibility achieve theoretically 100% internal quantum efficiency devices. In recent past, various classes been reported, possessing a beautiful structural variety allowed nicely obtain efficient photo- electroluminescence high colour purity red, green blue (RGB) portions visible spectrum. addition, achievement emission beyond range towards ultraviolet (UV) near infrared (NIR) regions was also challenged. By employing emitters OLEDs, remarkably device performances were demonstrated, square planar platinum(II) bearing π-conjugated chromophoric ligands playing key role respect. this contribution, most promising trends field platinum will be reviewed discussed. particular, importance proper molecular design underpins successful improved photophysical features enhanced highlighted. Special emphasis devoted those systems employed PhOLEDs.

Language: Английский

Citations

157

The key role of R–NHC coupling (R = C, H, heteroatom) and M–NHC bond cleavage in the evolution of M/NHC complexes and formation of catalytically active species DOI Creative Commons
Victor M. Chernyshev, Ekaterina A. Denisova, Dmitry B. Eremin

et al.

Chemical Science, Journal Year: 2020, Volume and Issue: 11(27), P. 6957 - 6977

Published: Jan. 1, 2020

Main types of the M–NHC bond transformations and their impact on activity stability M/NHC catalytic systems are considered.

Language: Английский

Citations

109

Silicon‐Derived Singlet Nucleophilic Carbene Reagents in Organic Synthesis DOI
Daniel L. Priebbenow

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(10), P. 1927 - 1946

Published: April 8, 2020

Abstract Over fifty years ago, the 1,2‐rearrangement of acylsilanes was first described by Adrian Brook and co‐workers. This rearrangement (now termed rearrangement) yields reactive silicon‐based singlet nucleophilic carbene (SNC) intermediates that participate in a variety chemical transformations including 1,2‐carbonyl addition, 1,4‐addition to electron‐deficient unsaturated bonds insertion into C−H O−H bonds. review aims cover historical literature recent advances with regard these valuable reagents highlight additional aspects related intriguing reactivity both oxocarbenium intermediates. magnified image

Language: Английский

Citations

97

Nitrogen fixation and transformation with main group elements DOI
Tong‐Tong Liu, Dan‐Dan Zhai, Bing‐Tao Guan

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(10), P. 3846 - 3861

Published: Jan. 1, 2022

In this tutorial, we introduced the fundamental aspects of nitrogen fixation, summarized recent progresses with main group elements and tried to make clear clue for further developments.

Language: Английский

Citations

52