Construction of 2-Amino-2′-ketonyl Biaryls via Acid-Mediated Ring Opening of 9H-Fluoren-9-ols with Organic Azides

2021 ◽  
Author(s):  
Shan Yang ◽  
Biqiong Hong ◽  
Jia Feng ◽  
Zhenhua Gu
Keyword(s):  
Ring Opening ◽  
Organic Azides

1,3,4-Trisubtituted-1,2,3-Triazol-5-ylidene 'Click' Carbene Ligands: Synthesis, Catalysis and Self-Assembly

2011 ◽  
Vol 64 (8) ◽  
pp. 1118 ◽  
Author(s):  
James D. Crowley ◽  
Ai-Lan Lee ◽  
Kelly J. Kilpin
Keyword(s):  
Metal Complexes ◽  
Self Assembly ◽  
Ring Opening ◽  
Click Reaction ◽  
Heterocyclic Carbenes ◽  
Terminal Alkynes ◽  
Carbene Ligands ◽  
Organic Azides ◽  
Self Assembled ◽  
Rapid Generation

This review examines the use of the Cu(I)-catalyzed 1,3-cycloaddition of organic azides with terminal alkynes (the CuAAC ‘click’ reaction) for development of a novel family of abnormal/mesoionic N-heterocyclic carbenes and their corresponding metal complexes. These 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have donor properties that are intermediate between the traditional Arduengo-type imidazol-2-ylidenes and more highly σ-donating abnormal carbenes, such as imidazol-4-ylidenes or pyrazolin-4-ylidenes. Metal complexes of the 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes have been used as catalysts for a variety of reactions including the CuAAC cycloaddition, Pd cross-couplings, and ring closing/ring opening metathesis. Additionally, ‘click’ carbene ligands have been used to generate self-assembled metallo-macrocycles and novel photosensitizers. The mild, modular CuAAC approach to these ligands should allow the rapid generation of libraries of 1,3,4-trisubstituted-1,2,3-triazol-5-ylidenes that can be further exploited to generate novel catalysts, metallo-pharmaceuticals and materials.

scholarly journals DFT and AFIR study on the copper(i)-catalyzed mechanism of 5-enamine-trisubstituted-1,2,3-triazole synthesis via C–N cross-coupling and the origin of ring-opening of 2H-azirines

RSC Advances ◽  
2021 ◽  
Vol 11 (5) ◽  
pp. 2744-2755
Author(s):  
Fan Yu ◽  
Zhaoman Zhou ◽  
Jiajia Song ◽  
Yanying Zhao
Keyword(s):  
Ring Opening ◽  
Click Reaction ◽  
Cross Coupling ◽  
Terminal Alkynes ◽  
Organic Azides

The Cu(i)-catalyzed mechanism of 5-enamined-functionalized fully substituted 1,2,3-triazole synthesis was rationalized by interrupted copper(i)-catalyzed terminal alkynes and organic azides click reaction (CuAAC).

Amino-functional polyethers: versatile, stimuli-responsive polymers

2020 ◽  
Vol 11 (24) ◽  
pp. 3940-3950 ◽  
Author(s):  
Patrick Verkoyen ◽  
Holger Frey
Keyword(s):  
Ring Opening ◽  
Review Article ◽  
Stimuli Responsive ◽  
New Class ◽  
Stimuli Responsive Polymers ◽  
Responsive Polymers

Amino-functional polyethers have emerged as a new class of “smart”, i.e. pH- and thermoresponsive materials. This review article summarizes the synthesis and applications of these materials, obtained from ring-opening of suitable epoxide monomers.

Reversible Oxidative-Addition and Reductive-Elimination of Thiophene from a Titanium Complex and Its Thermally-Induced Hydrodesulfurization Chemistry

2019 ◽  
Author(s):  
Alejandra Gomez-Torres ◽  
J. Rolando Aguilar-Calderón ◽  
Carlos Saucedo ◽  
Aldo Jordan ◽  
Alejandro J. Metta-Magaña ◽  
...  
Keyword(s):  
Dft Calculations ◽  
Ring Opening ◽  
Thiophene Ring ◽  
Oxidative Addition ◽  
Reductive Elimination ◽  
Thermally Induced ◽  
Titanium Complex

<p>The masked Ti(II) synthon (<sup>Ket</sup>guan)(<i>η</i><sup>6</sup>-Im<sup>Dipp</sup>N)Ti (<b>1</b>) oxidatively adds across thiophene to give ring-opened (<sup>Ket</sup>guan)(Im<sup>Dipp</sup>N)Ti[<i>κ</i><sup>2</sup>-<i>S</i>(CH)<sub>3</sub><i>C</i>H] (<b>2</b>). Complex <b>2</b> is photosensitive, and upon exposure to light, reductively eliminates thiophene to regenerate <b>1</b> – a rare example of early-metal mediated oxidative-addition/reductive-elimination chemistry. DFT calculations indicate strong titanium π-backdonation to the thiophene π*-orbitals leads to the observed thiophene ring opening across titanium, while a proposed photoinduced LMCT promotes the reverse thiophene elimination from <b>2</b>. Finally, pressurizing solutions of <b>2 </b>with H<sub>2</sub> (150 psi) at 80 °C leads to the hydrodesulfurization of thiophene to give the Ti(IV) sulfide (<sup>Ket</sup>guan)(Im<sup>Dipp</sup>N)Ti(S) (<b>3</b>) and butane. </p>

Visible Light-Promoted Catalytic Ring-Opening Isomerization of 1,2-Disubstituted Cyclopropanols to Linear Ketones

2019 ◽  
Author(s):  
Marharyta V. Laktsevich-Iskryk ◽  
Nastassia A. Varabyeva ◽  
Volha V. Kazlova ◽  
Vladimir N. Zhabinskii ◽  
Vladimir A. Khripach ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Ring Opening ◽  
Radical Intermediates ◽  
Reaction Proceeds

In this article, we report a photocatalytic protocol for the isomerization of 1,2-disubstituted cyclopropanols to linear ketones. The reaction proceeds <i>via</i> radical intermediates and tolerates various functional groups.

Visible Light-Promoted Catalytic Ring-Opening Isomerization of 1,2-Disubstituted Cyclopropanols to Linear Ketones

2019 ◽  
Author(s):  
Marharyta V. Laktsevich-Iskryk ◽  
Nastassia A. Varabyeva ◽  
Volha V. Kazlova ◽  
Vladimir N. Zhabinskii ◽  
Vladimir A. Khripach ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Ring Opening ◽  
Radical Intermediates ◽  
Reaction Proceeds

In this article, we report a photocatalytic protocol for the isomerization of 1,2-disubstituted cyclopropanols to linear ketones. The reaction proceeds <i>via</i> radical intermediates and tolerates various functional groups.

A Recommender System for Inverse Design of Polycarbonates and Polyesters

2020 ◽  
Author(s):  
Nathaniel Park ◽  
Dmitry Yu. Zubarev ◽  
James L. Hedrick ◽  
Vivien Kiyek ◽  
Christiaan Corbet ◽  
...  
Keyword(s):  
Ring Opening ◽  
High Performance ◽  
Recommendation System ◽  
Polymeric Materials ◽  
Monomer Conversion ◽  
Design Strategy ◽  
Ring Opening Polymerization ◽  
Inverse Design ◽  
False Negatives ◽  
Accelerate Development

The convergence of artificial intelligence and machine learning with material science holds significant promise to rapidly accelerate development timelines of new high-performance polymeric materials. Within this context, we report an inverse design strategy for polycarbonate and polyester discovery based on a recommendation system that proposes polymerization experiments that are likely to produce materials with targeted properties. Following recommendations of the system driven by the historical ring-opening polymerization results, we carried out experiments targeting specific ranges of monomer conversion and dispersity of the polymers obtained from cyclic lactones and carbonates. The results of the experiments were in close agreement with the recommendation targets with few false negatives or positives obtained for each class.<br>

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