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Relevant academic research and scientific papers

α-Arylation of (hetero)aryl ketones in aqueous surfactant media

α-Arylation reactions can be performed in water, enabled by a designer surfactant,under mild conditions and in the absence of organic co-solvents. A multitude of aryl and heteroaryl ketones are amenable to coupling with functionalized aryl halides. Use of a lipophilic base that can gain entry to the micellar inner cores mediates enolization. In some cases, palladium loadings as low as 2500 ppm (0.25 mol%) are sufficient for coupling in a completely recyclable medium, exemplifying chemistry in water.

Mild, Aqueous α-Arylation of Ketones: Towards New Diversification Tools for Halogenated Metabolites and Drug Molecules

The palladium-catalysed aqueous α-arylation of ketones was developed and tested for a large variety of reaction partners. These mild conditions enabled the coupling of aryl/alkyl-ketones with N-protected halotryptophans, heterocyclic haloarenes, and challenging base-sensitive compounds. The synthetic potential of this new methodology for the diversification of complex bioactive molecules was exemplified by derivatising prochlorperazine. The methodology is mild, aqueous and flexible, representing a means of functionalizing a wide range of halo-aromatics and therefore has the potential to be extended to complex molecule diversification.

Phenoxy-Linked Mesoionic Triazol-5-ylidenes as Platforms for Multinuclear Transition Metal Complexes

The preparation and full characterization of a variety of mono- ([L1-H]), di- ([L2-H2], [L2A-H2]), and tri- ([L3-H3]) 1,2,3-triazolium salts constructed form "clicked" hydroxybenzene derivatives are reported. Deprotonation with potassium hexamethyldisilazide, followed by in situ metalation, allowed for the synthesis of a series of mono- (L1·[M]), di- (L2·[M]2, L2·[M]2), and trinuclear (L3·[M]3) group 9-11 (M = [Rh(CO)2Cl], [Pd(allyl)Cl], and [AuCl]) triazol-5-ylidene metal complexes. In solution, all metal complexes feature symmetrical patterns displaying C2 and C3 fold axes when supported by di- and tritriazol-5-ylidene ligands. The vibration frequencies of Ln·[Rh(CO)2Cl]n (n = 1-3) complexes indicate that the electron-donor properties of the new ligands are comparable to those for previously reported MIC complexes and superior to classical NHCs. Prompting coordination of the vicinal phenoxy group to the metal centers proved unsuccessful after treatment of the Ln·[Rh(CO)2Cl]n and Ln·[Pd(allyl)Cl]n (n = 1-3) precursors with AgBF4; the expected chelated cationic complexes were highly unstable, indicating a weak or no coordination availability through the oxygen atom. Crystal structures of the complexes L1·[AuI] and L2A·[Pd(allyl)I]2 illustrated the metal center geometrical environment and confirmed the lack of coordination through the phenoxy moiety of the ligand. Preliminary catalytic trials established the enhanced performance of di- and trimetallic palladium complexes in cross-coupling reactions and the intramolecular cyclization of enynes catalyzed by gold complexes.

Versatile O- and S-functionalized 1,2,3-triazoliums: Ionic liquids for the Baylis-Hillman reaction and ligand precursors for stable MIC-transition metal complexes

The efficient synthesis of O- and S-functionalized 1,2,3-triazoliums is reported. Owing to their physical properties, these cations are efficient ionic liquids for Baylis-Hillman addition under mild reaction conditions. Simultaneously, the functionalizati

A new class of "electro-acid/base"-induced reversible methyl ketone colour switches

Methyl ketone has been designed as a switching unit for electrically addressable molecular colour switches. A newly proposed mechanism of "electro-acid/base" (radical ions)-induced intermolecular proton transfer for the colour switch is proven clearly by cyclic voltammetry (CV), X-ray photoelectron spectroscopy (XPS), infrared spectroscopy (IR) and in situ UV-Vis spectroscopy. A dramatic spectral absorption shift (about 291 nm) is observed during the switching, and blue, yellow and green colours are obtained by adjusting the substituents on the methyl ketone-bridged unit. The in situ "electro-acid/base" is far more convenient than the conventional chemical stimulus of acids or bases for the manipulation of the molecular switching properties. This new switching method and molecular structure manipulation will inspire and accelerate the further development of broad switching materials and applications in ultrathin flexible displays, etc.

The facile synthesis of α-aryl-α-hydroxy esters via one-pot vicarious nucleophilic substitution and oxidation

The anion produced by the vicarious nucleophilic substitution reaction of nitroarenes and α-chloro esters is hydroxylated by the action of air and benzaldehyde, thereby producing α-hydroxy esters.

A NOVEL NUCLEOPHILIC SUBSTITUTION OF THE FORMYL GROUP IN p-NITROBENZALDEHYDE WITH SOME CARBANIONS

p-Nitrobenzaldehyde reacts with some active methylene compounds in the presence of a strong base at low temperatures to give p-substituted nitrobenzenes by the two-step course involving the initial formation of the aldol adducts and the subsequent displacement of the carbinol moieties with excess carbanions.