Waste-Free Solid-State Organic Syntheses: Solvent-Free Alkylation, Heterocyclization, and Azo-Coupling Reactions.

ChemInform ◽  
2007 ◽  
Vol 38 (48) ◽  
Author(s):  
Ehab Abdel-Latif ◽  
Mohamed A. Metwally
Keyword(s):  
Solid State ◽  
Solvent Free ◽  
Coupling Reactions ◽  
Azo Coupling ◽  
Organic Syntheses

scholarly journals A Novel Electromagnetic Mill Promoted Mechanochemical Solid-State Suzuki–Miyaura Cross-Coupling Reactions: Ultra-Low Catalyst Loading without Molecular Dispersants

2021 ◽  
Author(s):  
Xin Li ◽  
Yunxia Liu ◽  
Lizhi Zhang ◽  
Yunhui Dong ◽  
Qing Liu ◽  
...  
Keyword(s):  
Solid State ◽  
Chemical Space ◽  
Cross Coupling ◽  
Solvent Free ◽  
Bioactive Molecules ◽  
Catalyst Loading ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Metal Catalyzed ◽  
High Yields

Abstract The Nobel-prize-winning Suzuki-Miyaura cross-coupling(SMC) is a practical and attractive strategy for the construction of C-C bonds in both academic and industrial settings. However, the development of solid-state SMC reactions remains extremely scarce. Herein, we report the first electromagnetic mill(EMM) promoted solid-state SMC reaction using ultra-low palladium loading(0.05 mol%) without any molecular dispersants. This protocol exhibits substantially broadened substrate scope, good functional groups tolerance and efficient gram-scale synthesis, especially, provides relative high yields. The utility of this strategy was exemplified in the modification of photoluminescence molecules, cross-coupling of slightly soluble compound and synthesis of several important bioactive molecules. Furthermore, the XPS analyses on the oxidation state changes of palladium catalyst suggest the involvement of PdI intermediate which might be the active catalytic species. This solvent-free solid-state EMM-SMC was potential developed into industrially attractive and environmentally friendly routes, and the EMM system developed in this study could unlock broad areas of chemical space for solvent-free solid-state metal-catalyzed syntheses of valuable targets in various scientific fields.

Withdrawal Notice: Recent Advances in Sonogashira Cross-Coupling Reactions Under Solvent-Free Conditions

2020 ◽  
Vol 24 ◽  
Author(s):  
Teng Wang ◽  
Zongrui Liu ◽  
Songlin Wang ◽  
Esmail Vessally
Keyword(s):  
Organic Chemistry ◽  
Editorial Policy ◽  
Cross Coupling ◽  
Solvent Free ◽  
Coupling Reactions ◽  
Editorial Policies ◽  
Cross Coupling Reactions ◽  
Recent Advances ◽  
Solvent Free Conditions ◽  
Copyright Permission

The article has been withdrawn at the request of editor of the journal Current Organic Chemistry: Bentham Science apologizes to the readers of the journal for any inconvenience this may have caused. The Bentham Editorial Policy on Article Withdrawal can be found at https://benthamscience.com/editorial-policies-main.php BENTHAM SCIENCE DISCLAIMER: It is a condition of publication that manuscripts submitted to this journal have not been published and will not be simultaneously submitted or published elsewhere. Furthermore, any data, illustration, structure or table that has been published elsewhere must be reported, and copyright permission for reproduction must be obtained. Plagiarism is strictly forbidden, and by submitting the article for publication the authors agree that the publishers have the legal right to take appropriate action against the authors, if plagiarism or fabricated information is discovered. By submitting a manuscript, the authors agree that the copyright of their article is transferred to the publishers if and when the article is accepted for publication.

scholarly journals Convenient Access to Functionalized Non-Symmetrical Atropisomeric 4,4′-Bipyridines

Compounds ◽  
2021 ◽  
Vol 1 (2) ◽  
pp. 58-74
Author(s):  
Emmanuel Aubert ◽  
Emmanuel Wenger ◽  
Paola Peluso ◽  
Victor Mamane
Keyword(s):  
Solid State ◽  
Intermolecular Interactions ◽  
Medicinal Chemistry ◽  
Crystal Packing ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Halogen Bonds ◽  
Cross Coupling Reactions ◽  
Cyano Groups ◽  
Post Functionalization

Non-symmetrical chiral 4,4′-bipyridines have recently found interest in organocatalysis and medicinal chemistry. In this regard, the development of efficient methods for their synthesis is highly desirable. Herein, a series of non-symmetrical atropisomeric polyhalogenated 4,4′-bipyridines were prepared and further functionalized by using cross-coupling reactions. The desymmetrization step is based on the N-oxidation of one of the two pyridine rings of the 4,4′-bipyridine skeleton. The main advantage of this methodology is the possible post-functionalization of the pyridine N-oxide, allowing selective introduction of chlorine, bromine or cyano groups in 2- and 2′-postions of the chiral atropisomeric 4,4′-bipyridines. The crystal packing in the solid state of some newly prepared derivatives was analyzed and revealed the importance of halogen bonds in intermolecular interactions.

Room Temperature Solvent-Free Synthesis of Monodisperse Magnetite Nanocrystals

2006 ◽  
Vol 6 (3) ◽  
pp. 852-856 ◽  
Author(s):  
X. R. Ye ◽  
C. Daraio ◽  
C. Wang ◽  
J. B. Talbot ◽  
S. Jin
Keyword(s):  
Oleic Acid ◽  
Solid State ◽  
Large Scale ◽  
Room Temperature ◽  
Solvent Free ◽  
Two Dimensional ◽  
New Process ◽  
High Boiling Point ◽  
Magnetite Nanocrystals ◽  
Solvent Free Synthesis

We have successfully demonstrated a facile, solvent-free synthesis of highly crystalline and monodisperse Fe3O4 nanocrystallites at ambient temperature avoiding any heating. Solid state reaction of inorganic Fe(II) and Fe(III) salts with NaOH was found to produce highly crystalline Fe3O4 nanoparticles. The reaction, if carried out in the presence of surfactant such as oleic acid–oleylamine adduct, generated monodisperse Fe3O4 nanocrystals extractable directly from the reaction mixture. The extracted nanoparticles were capable of forming self-assembled, two-dimensional and uniform periodic array. The new process utilizes inexpensive and nontoxic starting materials, and does not require a use of high boiling point and toxic solvents, thus is amenable to an environmentally desirable, large-scale synthesis of nanocrystals.

scholarly journals Investigation of Solvatomorphism and Its Photophysical Implications for Archetypal Trinuclear Au3(1-Methylimidazolate)3

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4404
Author(s):  
Shengyang Guan ◽  
David C. Mayer ◽  
Christian Jandl ◽  
Sebastian J. Weishäupl ◽  
Angela Casini ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Density Functional ◽  
Bulk Material ◽  
Variable Temperature ◽  
Active Phase ◽  
Solvent Free ◽  
X Ray Diffraction ◽  
X Ray ◽  
Aurophilic Interactions

A new solvatomorph of [Au3(1-Methylimidazolate)3] (Au3(MeIm)3)—the simplest congener of imidazolate-based Au(I) cyclic trinuclear complexes (CTCs)—has been identified and structurally characterized. Single-crystal X-ray diffraction revealed a dichloromethane solvate exhibiting remarkably short intermolecular Au⋯Au distances (3.2190(7) Å). This goes along with a dimer formation in the solid state, which is not observed in a previously reported solvent-free crystal structure. Hirshfeld analysis, in combination with density functional theory (DFT) calculations, indicates that the dimerization is generally driven by attractive aurophilic interactions, which are commonly associated with the luminescence properties of CTCs. Since Au3(MeIm)3 has previously been reported to be emissive in the solid-state, we conducted a thorough photophysical study combined with phase analysis by means of powder X-ray diffraction (PXRD), to correctly attribute the photophysically active phase of the bulk material. Interestingly, all investigated powder samples accessed via different preparation methods can be assigned to the pristine solvent-free crystal structure, showing no aurophilic interactions. Finally, the observed strong thermochromism of the solid-state material was investigated by means of variable-temperature PXRD, ruling out a significant phase transition being responsible for the drastic change of the emission properties (hypsochromic shift from 710 nm to 510 nm) when lowering the temperature down to 77 K.

scholarly journals Mechanochemical and solvent-free assembly of zirconium-based metal–organic frameworks

2016 ◽  
Vol 52 (10) ◽  
pp. 2133-2136 ◽  
Author(s):  
Krunoslav Užarević ◽  
Timothy C. Wang ◽  
Su-Young Moon ◽  
Athena M. Fidelli ◽  
Joseph T. Hupp ◽  
...  
Keyword(s):  
Solid State ◽  
High Temperatures ◽  
Self Assembly ◽  
Metal Organic Frameworks ◽  
Accelerated Aging ◽  
Solvent Free ◽  
Catalytically Active ◽  
Metal Organic ◽  
Strong Acids ◽  
Zirconium Metal

Mechanochemistry and accelerated aging are new routes to zirconium metal–organic frameworks, yielding UiO-66 and catalytically active UiO-66-NH2 accessible on the gram scale through mild solid-state self-assembly, without strong acids, high temperatures or excess reactants.

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