Ketone hydrogenation catalyzed by a new iron(ii)–PNN complex

2016 ◽  
Vol 6 (12) ◽  
pp. 4428-4437 ◽  
Author(s):  
B. Butschke ◽  
M. Feller ◽  
Y. Diskin-Posner ◽  
D. Milstein
Keyword(s):  
Hydride Complex ◽  
Mild Conditions ◽  
Ketone Hydrogenation ◽  
Proton Migration

A dearomatized Fe(ii)–hydride complex mediates the hydrogenation of enolizable ketones under very mild conditions. Deactivation occursviaintramolecular proton migration.

Hydrosilylation of Aldehydes and Ketones Catalyzed by an N-Heterocyclic Carbene-Nickel Hydride Complex under Mild Conditions

2012 ◽  
Vol 354 (14-15) ◽  
pp. 2619-2624 ◽  
Author(s):  
Linus P. Bheeter ◽  
Mickaël Henrion ◽  
Lydia Brelot ◽  
Christophe Darcel ◽  
Michael J. Chetcuti ◽  
...  
Keyword(s):  
Hydride Complex ◽  
Mild Conditions ◽  
Nickel Hydride ◽  
Aldehydes And Ketones

Catalytic reduction of dimethylsulfoxide by molecular hydrogen using rhodium(III) complexes

1969 ◽  
Vol 47 (24) ◽  
pp. 4521-4526 ◽  
Author(s):  
B. R. James ◽  
F. T. T. Ng (Miss) ◽  
G. L. Rempel
Keyword(s):  
Molecular Hydrogen ◽  
Catalytic Reduction ◽  
Catalytic Efficiency ◽  
Hydride Complex ◽  
Mild Conditions ◽  
Kinetics Of

Dimethylsulfoxide is reduced by molecular hydrogen under mild conditions to dimethylsulfide and water in the presence of rhodium(III) complexes as catalysts. The kinetics of the systems using RhCl3.3H2O and cis-RhCl3(Et2S)3 have been investigated, and a mechanism involving reduction of coordinated dimethylsulfoxide in a rhodium(III) hydride complex is postulated. The catalytic efficiency of the systems decreases slowly due to the production of inactive rhodium(I) species.

ChemInform Abstract: Hydrosilylation of Aldehydes and Ketones Catalyzed by an N-Heterocyclic Carbene-Nickel Hydride Complex under Mild Conditions.

ChemInform ◽  
2013 ◽  
Vol 44 (14) ◽  
pp. no-no
Author(s):  
Linus P. Bheeter ◽  
Mickael Henrion ◽  
Lydia Brelot ◽  
Christophe Darcel ◽  
Michael J. Chetcuti ◽  
...  
Keyword(s):  
Hydride Complex ◽  
Mild Conditions ◽  
Nickel Hydride ◽  
Aldehydes And Ketones

The Diorgano Dichalcogenides Addition to Benzyne under Mild Conditions

2007 ◽  
Author(s):  
Fabiano Toledo ◽  
Henrique Marques ◽  
João Comasseto ◽  
Cristiano Raminelli
Keyword(s):  
Mild Conditions

Dual-Function, Light Switchable Cobalt Catalysis via Active Site Metamorphosis

2019 ◽  
Author(s):  
Enrico Bergamaschi ◽  
Frédéric Beltran ◽  
Christopher Teskey
Keyword(s):  
Visible Light ◽  
Active Site ◽  
Catalytic Site ◽  
Dual Function ◽  
Catalytic Systems ◽  
Hydride Complex ◽  
Dual Functional ◽  
Multiple Processes ◽  
Olefin Migration

<p></p><p></p><p>Switchable catalysis offers opportunities to control the rate or selectivity of a reaction <i>via</i> a stimulus such as pH or light. However, few examples of switchable catalytic systems that can facilitate multiple processes exist. Here we report a rare example of such dual-functional, switchable catalysis. Featuring an easily prepared, bench-stable cobalt(I) hydride complex in conjunction with pinacolborane, we can completely alter the reaction outcome between two widely employed transformations – olefin migration and hydroboration – with visible light as the sole trigger. This dichotomy arises from ligand photodissociation which leads to metamorphosis of the active catalytic site, resulting in divergent mechanistic pathways.</p><p></p><p></p>

Pt-Pd Nanoalloy for the Unprecedented Activation of Carbon-Fluorine Bond at Low Temperature

2019 ◽  
Author(s):  
Raghu Nath Dhital ◽  
keigo nomura ◽  
Yoshinori Sato ◽  
Setsiri Haesuwannakij ◽  
Masahiro Ehara ◽  
...  
Keyword(s):  
Activation Energy ◽  
Low Temperature ◽  
Dft Calculations ◽  
Bond Activation ◽  
Mild Conditions ◽  
Selective Transformation ◽  
Rate Determining Step ◽  
Highly Active ◽  
Harsh Conditions ◽  
Reaction Profile

Carbon-Fluorine (C-F) bonds are considered the most inert organic functionality and their selective transformation under mild conditions remains challenging. Herein, we report a highly active Pt-Pd nanoalloy as a robust catalyst for the transformation of C-F bonds into C-H bonds at low temperature, a reaction that often required harsh conditions. The alloying of Pt with Pd is crucial to activate C-F bond. The reaction profile kinetics revealed that the major source of hydrogen in the defluorinated product is the alcoholic proton of 2-propanol, and the rate-determining step is the reduction of the metal upon transfer of the <i>beta</i>-H from 2-propanol. DFT calculations elucidated that the key step is the selective oxidative addition of the O-H bond of 2-propanol to a Pd center prior to C-F bond activation at a Pt site, which crucially reduces the activation energy of the C-F bond. Therefore, both Pt and Pd work independently but synergistically to promote the overall reaction

Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

2020 ◽  
Author(s):  
Birgit Meindl ◽  
Katharina Pfennigbauer ◽  
Berthold Stöger ◽  
Martin Heeney ◽  
Florian Glöcklhofer
Keyword(s):  
Wittig Reaction ◽  
Condensation Reaction ◽  
Synthetic Methods ◽  
Anthracene Derivative ◽  
Double Ring ◽  
Mild Conditions ◽  
Wide Range ◽  
Anthracene Derivatives

Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions followed by a deprotection and intramolecular double ring-closing condensation reaction. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach.<br>

SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates and Sulfonamides from S(VI) Fluorides

2020 ◽  
Author(s):  
Subham Mahapatra ◽  
Cristian P. Woroch ◽  
Todd W. Butler ◽  
Sabrina N. Carneiro ◽  
Sabrina C. Kwan ◽  
...  
Keyword(s):  
Room Temperature ◽  
Medicinal Chemistry ◽  
Mild Conditions ◽  
Broad Array

<p><br></p> <p>A method to activate sulfamoyl fluorides, fluorosulfates, and sulfonyl fluorides with calcium triflimide, and DABCO for SuFEx with amines is described. The reaction was applied to a diverse set of sulfamides, sulfamates, and sulfonamides at room temperature under mild conditions. Additionally, we highlight the application of this transformation to parallel medicinal chemistry to generate a broad array of nitrogen-based S(VI) compounds. </p>

SuFEx Activation with Ca(NTf2)2: A Unified Strategy to Access Sulfamides, Sulfamates and Sulfonamides from S(VI) Fluorides

2020 ◽  
Author(s):  
Subham Mahapatra ◽  
Cristian P. Woroch ◽  
Todd W. Butler ◽  
Sabrina N. Carneiro ◽  
Sabrina C. Kwan ◽  
...  
Keyword(s):  
Room Temperature ◽  
Medicinal Chemistry ◽  
Mild Conditions ◽  
Broad Array

<p><br></p> <p>A method to activate sulfamoyl fluorides, fluorosulfates, and sulfonyl fluorides with calcium triflimide, and DABCO for SuFEx with amines is described. The reaction was applied to a diverse set of sulfamides, sulfamates, and sulfonamides at room temperature under mild conditions. Additionally, we highlight the application of this transformation to parallel medicinal chemistry to generate a broad array of nitrogen-based S(VI) compounds. </p>

Microwave-Assisted Decarbonylation of Biomass-Derived Aldehydes Using Pd-Doped Hydrotalcites

2019 ◽  
Author(s):  
Nan An ◽  
Diana Ainembabazi ◽  
Kavya Samudrala ◽  
Christopher Reid ◽  
Kare Wilson ◽  
...  
Keyword(s):  
Heterogeneous Catalysts ◽  
Reaction Times ◽  
Inverse Correlation ◽  
Mulliken Charge ◽  
Metal Leaching ◽  
Carbonyl Carbon ◽  
Mild Conditions ◽  
Microwave Assisted ◽  
Biomass Processing ◽  
Alcohol Dehydrogenation

<p>Here we report the synthesis, characterization and activity of tunable Pd-doped hydrotalcites (Pd-HTs) for the decarbonylation of furfural, hydroxymethylfurfural (HMF), aromatic and aliphatic aldehydes under microwave conditions. The decarbonylation activity reported is a notable improvement over prior heterogeneous catalysts for this process. Furfural decarbonylation is optimized in a benign solvent compatible with biomass processing - ethanol, under relatively mild conditions and short reaction times. HMF selectively affords excellent yields of furfuryl alcohol with no humin formation, but longer reaction can also afford furan via tandem alcohol dehydrogenation and decarbonylation. Yields of substituted benzaldehydes are related to calculated Mulliken charge of the carbonyl carbon. The activity and selectivity differences can be traced to loading-dependent differences in Pd speciation on the catalysts. Poisoning studies show inverse correlation between Pd loading and metal leaching: Pd-HTs with lowest Pd loading, which consist of highly dispersed and oxidized Pd species, operate heterogeneously with negligible metal leaching. Recycling experiments are consistent with this trend, offering potential for further optimization to improve robustness.</p>

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