85248-68-6

Upstream product

• 100-42-5 styrene 
• 580-13-2 2-bromonaphthalene 
• 538-51-2 benzylidene phenylamine 
• 91-57-6 2-Methylnaphthalene 
• 35160-95-3 (2-naphthalenylmethyl)triphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 134988-30-0 benzyldibutyltelluronium bromide 
• 66-99-9 β-naphthaldehyde 
• 27854-69-9 trans-1-<2-(1-bromonaphthyl)>-2-phenylethene 
• 32316-92-0 naphthalene-2-boronic acid 
• 93-09-4 naphthalene-2-carboxylate 
• 57647-89-9 isopropenyl 2-naphthoate 

Downstream Products

• 121012-86-0 trans-β-fluoro-β-naphth-2-ylstyrene 
• 121072-44-4 cis-β-fluoro-β-naphth-2-ylstyrene 
• 195-19-7 benzo[c]phenathrene 
• 36707-32-1 1-(1-naphthyl)-2-phenylethane 
• 80663-26-9 9,10-dihydro-3,4-benzophenanthrene 
• 2039-70-5 (Z)-1-(2-naphthyl)-2-phenylethene 
• 85248-69-7 1-phenyl-2-(2-naphthyl)ethylene radical anion 
• 644-13-3 C₆H₅COC₁₀H₇ 
• 88657-73-2 tricarbonyl(η4-2-styrylnaphthalene)iron 
• 65648-94-4 1-(naphthalen-2-yl)-2-phenylethane-1,2-dione 
• 121012-85-9 α-bromo-β-fluoro-β-naphth-2-ylstyrene 

Relevant academic research and scientific papers

Xanthate-mediated synthesis of (E)-alkenes by semi-hydrogenation of alkynes using water as the hydrogen donor

Semi-hydrogenation of alkynes is one of the most widely used methods for obtaining alkenes in laboratory preparation and in industry. Transition metal catalysts have been extensively studied for this transformation, but the tolerance of functional groups, such as pyridine,-OH,-NH2,-Bpin, and halides, and the toxicity of the trace amount of transition metal catalysts are still highly challenging. In this study, we report a general and robust strategy to achieve the semi-hydrogenation of alkynes using inexpensive and commercially available xanthate as the mediator. Mechanism studies support a non-radical process and H2O acts as the hydrogen donor.

Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes

This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis

Aza-peterson olefinations: Rapid synthesis of (E)-alkenes

An aza-Peterson olefination methodology to access 1,3-dienes and stilbene derivatives from the corresponding allyl- or benzyltrimethylsilane is described. Silanes can be deprotonated using Schlosser's base and added to N -phenyl imines or ketones to directly give the desired products in high yields.

N-Heterocyclic carbene palladium (II)-pyridine (NHC-Pd (II)-Py) complex catalyzed heck reactions

A mild, efficient, and practical catalytic system for the synthesis of highly privileged stilbene pharmacophores is reported. This system uses N-heterocyclic carbene palladium (II) Pyridine (NHC-Pd (II)-Py) complex to catalyze the formation of carbon-carbon bonds between olefin derivatives and various bromide. This simple, gentle and user-friendly method can offer a variety of stilbene products in excellent yields under solvent-free condition. And its scale-up reaction has excellent yield and this system can be applied to industrial fields. The utility of this method is highlighted by its universality and modular synthesis of a series of bioactive molecules or important medical intermediates.

Dinuclear cobalt complex-catalyzed stereodivergent semireduction of alkynes: Switchable selectivities controlled by H2O

Catalytic semireduction of internal alkynes to alkenes is very important for organic synthesis. Although great success has been achieved in this area, switchable Z/E stereoselectivity based on a single catalyst for the semireduction of internal alkynes is a longstanding challenge due to the multichemo- and stereoselectivity, especially based on less-expensive earth-abundant metals. Herein, we describe a switchable semireduction of alkynes to (Z)- or (E)-alkenes catalyzed by a dinuclear cobalt complex supported by a macrocyclic bis pyridyl diimine (PDI) ligand. It was found that cis-reduction of the alkyne occurs first and the Z-E alkene stereoisomerization process is formally controlled by the amount of H2O, since the concentration of H2O may influence the catalytic activity of the catalyst for isomerization. Therefore, this protocol provides a facile way to switch to either the (Z)- or (E)-olefin isomer in a single transformation by adjusting the amount of water.

METHODS OF ARENE ALKENYLATION

The present disclosure provides for a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. For example, the present disclosure provides for method of making arenes or substituted arenes, in particular stilbene and stilbene derivatives, from a reaction of an optionally substituted arene and/or optionally substituted styrene. The reaction includes a Rh catalyst or Rh pre-catalyst material and an oxidant, where the Rh catalyst or Rh catalyst formed Rh pre-catalyst material selectively functionalizes CH bond on the arene compound (e.g., benzene or substituted benzene).

Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

Mizoroki-Heck Reaction of Unstrained Aryl Ketones via Ligand-Promoted C-C Bond Olefination

Mizoroki-Heck reaction of unstrained aryl ketone with acrylate/styrene is accomplished via palladium-catalyzed ligand-promoted C-C bond cleavage. Various (hetero)aryl ketones are compatible in the reaction, affording the alkene product in good to excellent yields. Further applications in the late-stage olefination of some drugs, natural products, and fragrance-derived aryl ketones demonstrate the synthetic utility of this protocol. By employing ketone as both the directing group and the leaving group, 1,2-bifunctionalization is achieved via sequential ortho-C-H alkylation/ipso-Heck olefination.

Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation

Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we report a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. The reaction is successful with several functional groups on both the arene and the olefin including fluoride, chloride, trifluoromethyl, ester, nitro, acetate, cyanide, and ether groups. Reactions of monosubstituted arenes are selective for alkenylation at the meta and para positions, generally with approximately 2:1 selectivity, respectively. Resveratrol and (E)-1,2,3-trimethoxy-5-(4-methoxystyryl)benzene (DMU-212) are synthesized by this single-step approach in high yield. Comparison with palladium catalysis showed that rhodium catalysis is more selective for meta-functionalization for monosubstituted arenes and that the Rh catalysis has better tolerance of halogen groups.

A Bidentate Ru(II)-NC Complex as a Catalyst for Semihydrogenation of Alkynes to (E)-Alkenes with Ethanol

Four Ru(II)-NC complexes were tested as catalysts for semihydrogenation of internal alkynes to (E)-alkenes with ethanol, and the complex {(C5H4N)(C6H4)}RuCl(CO)(PPh3)2 (1a) showed the highest activity. The reactions proceeded well with 1 mol % catalyst loading and 0.1 equiv of t-BuONa at 110 °C for 1 h, and 32 alkenes were synthesized with excellent E:Z selectivity. This is the first ruthenium-catalyzed semihydrogenation of internal alkynes to (E)-alkenes using ethanol as the hydrogen donor.