77150-94-8

Upstream product

• 253684-23-0 1,1-dibromo-2-(3-methoxyphenyl)ethene 
• 105281-53-6 (E)-trimethyl<2-(3-methoxyphenyl)ethenyl>silane 
• 107415-80-5 ω-Brom-3-methoxy-styrol 
• 6099-04-3 3-methoxycinnamic acid 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 74-95-3 1,1-dibromomethane 
• 591-31-1 3-methoxy-benzaldehyde 
• 626-20-0 3-methoxystyrene 
• 6099-04-3 trans-3-methoxycinnamic acid 
• 766-85-8 3-methoxy-1-iodobenzene 
• 14275-61-7 (E)-1,2-bis(tri-n-butylstannyl)ethene 
• 2398-37-0 3-methoxyphenyl bromide 

Downstream Products

• 1334164-63-4 (E)-N-phenyl-N-(3-methoxystyryl)aniline 
• 88348-41-8 2-(3-methoxyphenyl)-2H-chromene 

Relevant academic research and scientific papers

The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis

Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.

Transition-Metal-Free α-Vinylation of Enolizable Ketones with β-Bromostyrenes

An α-vinylation of enolizable ketones has been developed by using β-bromostyrenes and a KOtBu/NMP system. β,γ-Unsaturated ketones of E configuration were obtained in excellent yield and selectivity. Further synthetic possibilities are highlighted by one-pot functionalization via trapping of intermediate dienolates with alkyl, allyl, benzyl, and propargyl halides to generate quaternary centers. The reported transformation is believed to involve phenylacetylene and propargylic alcohol derivatives.

Palladium-Catalyzed Domino Reaction for Stereoselective Synthesis of Multisubstituted Olefins: Construction of Blue Luminogens

The first Pd-catalyzed multicomponent reaction of aryl iodides, alkenyl bromides, and strained alkenes has been developed, which allowed us to synthesize a variety of multisubsituted olefins in yields of 45-96% with excellent stereoselectivity. The configuration of the product was controlled by the configuration of the alkenyl bromides. Moreover, this practical methodology employing readily available substrates was found to be tolerant to a wide range of functional groups. Fifty six examples of highly stereoselective tri- or tetrasubstituted olefins have been successfully synthesized via this methodology. Most of the synthesized tetrasubstituted olefins are good aggregation-induced emission (AIE) luminogens.

Palladium-Catalyzed Decarboxylative γ-Olefination of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Vinyl Halides

This study explores a Pd-catalyzed decarboxylative Heck-type Csp3-Csp2 coupling reaction of 2,5-cyclohexadiene-1-carboxylic acid derivatives with vinyl halides to provide γ-olefination products. The olefinated 1,3-cyclohexadienes can be further oxidized to produce meta-alkylated stilbene derivatives. Additionally, the conjugated diene products can also undergo a Diels-Alder reaction to produce a bicyclo[2.2.2]octadiene framework.

Decarboxylative bromination of α,β-unsaturated carboxylic acids via an anodic oxidation

A novel bromination of α,β-unsaturated carboxylic acids was developed via a decarboxylation by virtue of a direct anodic electro-oxidation. In this method, ammonium bromide was employed as a bromine source and the reaction features transition-metal-free, short time, and no additional supporting electrolyte.

Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides

This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy-to-operate nickel-catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional-group tolerance. The nickel-catalytic system displays good chemoselectivity between the two C(sp2)-halide coupling partners, thus demonstrating a mechanistic pathway distinct from other stepwise protocols.

New one-pot synthesis of (E)-β-aryl vinyl halides from styrenes

A new, efficient protocol for the highly stereoselective one-pot synthesis of (E)-β-aryl vinyl iodides and (￡)-β-aryl vinyl bromides from styrenes based on sequential ruthenium-catalyzed silylative coupling-N-halosuccinimide-mediated halodesilylation reactions is reported.

Facile and stereoselective synthesis of (E)-vinyl bromides by microwave-induced reaction of 1,1-dibromoalkenes using a diethyl phosphonate/EtONa/EtOH system

(E)-Vinyl bromides were readily prepared from 1,1-dibromoalkenes by microwave irradiation within 1 min using a diethyl phosphonate/EtONa/EtOH system. This method utilizes cheap and environmentally friendly reagents, requires only a short reaction time, and gives (E)-vinyl bromides in high stereoselectivities and high yields.

Palladium(0) Catalyzed Coupling of trans-1,2-Bis(tri-n-butylstannyl)ethylene with Aromatic Halides: A convenient Synthesis of Substituted trans-β-Bromostyrenes

trans-β-Bromostyrenes have been conveniently prepared in moderate to high yield in a one-pot two-step sequence. trans-1,2-Bis(tri-n-butylstannyl)ethylene underwent a smooth palladium(0) catalyzed coupling reaction with 0.5 equivalents of aromatic bromide or iodide to furnish a trans-β-stannylstyrene.This intermediate vinyl stannane, without isolation, was then converted to the substituted trans-bromostyrene on treatment with molecular bromine.