10.1016/j.tetlet.2007.12.128
The research focuses on the radical [18F]fluoroarylation of various olefins using 4-[18F]fluorobenzenediazonium ions, offering a novel approach to synthesize radiopharmaceuticals containing a deactivated, 4-[18F]fluoro substituted phenyl group. The study demonstrates the methodology's suitability for the synthesis of 18F-labeled stilbenes, with stilbene 7 being synthesized within 80 minutes with a 30–45% overall radiochemical yield starting from [18F]fluoride. The experiments involved reacting 4-fluorobenzenediazonium tetrafluoroborate with substrates such as arecoline, ecgonidine methylate, and styrenes under optimized conditions using titanium(III)-chloride in dilute hydrochloric acid as a reductant. The analyses included determining radiochemical yields through reverse-phase high-performance liquid chromatography (RP-HPLC) with gradient elution and UV detection at 214 nm, as well as assessing diastereoselectivity in the synthesized products.
10.1021/jm010298j
The study focuses on the design, synthesis, and evaluation of trans-stilbene derivatives as potent and selective inhibitors of human cytochrome P450 1B1 (CYP1B1), an enzyme implicated in chemical carcinogenesis and estrogen metabolism. The researchers synthesized a series of trans-stilbene compounds containing a 3,5-dimethoxyphenyl moiety through an efficient solution phase synthetic pathway. These compounds were tested for their inhibitory activities on human cytochrome P450s, specifically CYP1A1, 1A2, and 1B1. The most selective and potent CYP1B1 inhibitor identified was 2,3′,4,5′-tetramethoxystilbene (7a). The study aimed to find compounds that could prevent mammary tumor formation by inhibiting CYP1B1-dependent estrogen metabolism, which may be valuable for the development of chemopreventive or therapeutic agents for cancer. The chemicals used in the study served as synthetic precursors for the stilbene derivatives and as tools to understand the structure-activity relationships of these compounds as CYP1B1 inhibitors.
10.1002/ejoc.201301757
The study presents a rhodium-catalyzed cross-coupling reaction between vinylarenes and arylaluminum reagents, which results in the formation of stilbene derivatives, π-conjugated organic materials of interest in organic synthesis. Key chemicals used include diethyl(phenyl)aluminum as the arylaluminum reagent, styrene as a representative vinylarene, and various ketones such as diisopropyl ketone, acetone, and pinacolone, which serve as additives that promote the reaction. The study also explores the use of different rhodium catalysts, including [RhCl(cod)]2, [Rh(OH)(cod)]2, and [Rh(OMe)(cod)]2, to optimize the reaction conditions and yield of stilbene products. The purpose of these chemicals is to facilitate an addition/elimination-type reaction that expands the scope of organic synthesis using organoaluminum reagents, which are known for their functional-group tolerance compared to other nucleophiles like organomagnesium and organolithium reagents.
10.1002/anie.201405996
The study introduces sulfenate anions as a new class of organocatalysts, demonstrating their ability to catalyze the conversion of benzyl halides into trans-stilbenes under basic conditions with yields up to 99%. The researchers hypothesized that sulfenate anions, known for their reactivity, could serve as catalysts based on their behavior in a palladium-catalyzed conversion of aryl benzyl sulfoxides into diaryl sulfoxides. They optimized the reaction conditions using benzyl phenyl sulfoxide as the catalyst precursor and KOtBu as the base in cyclopentyl methyl ether (CPME) solvent at 80°C. The study explored various benzyl halides, finding that benzyl chlorides were more effective than bromides. The scope of the transformation included substrates with alkyl, halide, and fluorine substituents, achieving good to excellent yields. Mechanistic studies supported the intermediacy of sulfenate anions and identified the deprotonated sulfoxide as the catalyst's resting state. The research also demonstrated the scalability of the reaction and the potential use of different sulfoxide precatalysts, including DMSO.
10.1021/ja01628a047
The research encompasses several studies focused on chemical reactions and synthesis. One study investigates the reactions of triphenylsilyllithium with stilbene and tolan, aiming to understand the products and mechanisms involved. Key chemicals include triphenylsilyllithium, stilbene, tolan, and ethylene glycol dimethyl ether. The study concludes that the reactions yield a variety of products, such as 1,2-bis-(triphenylsilyl)-1,2-diphenylethane and 1-triphenylsilyl-1,2,3,4-tetraphenylbutane, with the formation of these compounds influenced by reaction conditions and solvents. Another study prepares o-nitrophenylphosphonic acid from a mixture of nitrophenylphosphonic acid isomers using magnesium salts, highlighting the role of ortho substituents in inhibiting the formation of insoluble magnesium salts. This method allows for the isolation of pure o-nitrophenylphosphonic acid, which has been challenging to obtain through other means.
10.1021/ja044875f
This research aimed to detect and study the reactivity of palladium complexes, specifically Pd(bcope)(OTf)2 (where bcope is (C8H14)PCH2CH2P(C8H14)), using parahydrogen-induced polarization (PHIP) effect in NMR spectroscopy. The study demonstrated that the PHIP effect could be used to detect metal complexes without the need for enhancement of a hydride resonance, and it provided insights into the reactions of the palladium complex with alkynes, particularly the formation and transformation of intermediates and products such as cis- and trans-stilbene. The researchers observed that the PdCHPhCH2Ph group of the complex transforms most readily into trans-stilbene, confirming that hydride insertion is reversible and involves a discrete Pd(bcope)(PhCH=CHPh)(H)2 intermediate. The study concluded that PHIP is not limited to the study of metal dihydrides and can enhance the detection of organic components within a metal's ligand sphere, offering a new approach to map concerted catalytic hydrogenation by a palladium(II) bis-phosphine complex.
Xn, 
N
