92975-14-9

Upstream product

• 99-90-1 para-bromoacetophenone 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 75230-51-2 4-bromoacetophenone tosylhydrazone 
• 69151-18-4 1-bromo-4-(1-bromovinyl)benzene 
• 102402-62-0 3,4-Bis-(4-bromo-phenyl)-2,5-dihydro-thiophene 1,1-dioxide 
• 100990-01-0 3,4-Bis-(4-bromo-phenyl)-2,5-dihydro-thiophene 
• 58881-56-4 2,2'-thiobis[1-(4-bromophenyl)ethanone] 

Relevant academic research and scientific papers

Preparation method of conjugated diene compound

The invention belongs to the field of fine chemicals and relevant chemical technologies and provides a preparation method of a butadiene derivative. The preparation method comprises the following steps of by taking phenylacetylene and a derivative thereof as raw materials, under the actions of a metal catalyst and an additive, performing reaction in an anhydrous organic solvent, and converting thephenylacetylene and the derivative thereof to a 2,3-di-substituted-1,3-butadiene compound. The preparation method has the beneficial effects of being simple and convenient to operate and mild in condition, being environmental friendly, having the possibility of realizing industrialization, and preparing the butadiene compound with a higher yield. The butadiene compound synthesized by utilizing the method can perform further functionalization to obtain various compounds, and then the compounds are applied to development and study of natural products, functional materials and the fine chemicals.

Pd-catalyzed cross-coupling reactions of hydrazones: Regioselective synthesis of highly branched dienes

The regioselective formation of highly branched dienes is a challenging task. Design and exploration of alternative working models to achieve such a regioselectivity to accomplish highly branched dienes is considered to be a historical advancement of Heck reaction to construct branched dienes. On the basis of the utility of carbene transfer reactions, in the reaction of hydrazones with Pd(II) under oxidative conditions, we envisioned obtaining a Pd-bis-carbene complex with α-hydrogens, which can lead to branched dienes. Herein, we report a novel Pd-catalyzed selective coupling reaction of hydrazones in the presence of t-BuOLi and benzoquinone to form the corresponding branched dienes. The utility of the Pd catalyst for the cross-coupling reactions for synthesizing branched conjugated dienes is rare. The reaction is very versatile and compatible with a variety of functional groups and is useful in synthesizing heterocyclic molecules. We anticipate that this Pd-catalyzed cross-coupling reaction will open new avenues for synthesizing useful compounds.

Facile synthesis of dibranched conjugated dienes via palladium-catalyzed oxidative coupling of N-tosylhydrazones

A facile and highly regioselective Pd-catalyzed oxidative coupling of N-tosylhydrazones providing efficient access to 2,3-disubstituted-1,3-butadienes has been developed. This process features readily available starting materials and mild reaction conditions. Further transformations of the obtained dibranched 1,3-dienes, through Diels-Alder reactions and indene synthesis, are also demonstrated, which reveal their great potential for synthetic utility.

Direct one-pot synthesis of 2,3-diarylbuta-1,3-diene via self-coupling of acetophenones

A mild and straightforward route to 2,3-diarylbuta-1,3-diene is described here. By treatment with SmI2-Ac20, acetophe-none and its analogues underwent self-coupling reactions and subsequent elimination to give a series of 2,3-diarylbuta-1,3-dienes in moderate to good yields.

Palladium-catalyzed inter- and intramolecular coupling reactions of aryl and vinyl halides mediated by indium

(Chemical Equation Presented) Treatment of aryl and vinyl halides with 50 mol % of 100 mesh indium, 2.5 mol % of Pd-C, and 1.5 equiv of LiCl under mild conditions (DMF, 100°C, 1-3 h) could produce coupling products efficiently in good to excellent yields in which the Csp2-Csp2 bond was formed. This reagent worked equally well with both intermolecular and intramolecular coupling reactions, producing a variety of biaryls, 1,3-dienes, and cyclic compounds.

EFFICIENT PREPARATION OF POLYSUBSTITUTED 1,3-DIENES FROM α,α'-DIKETO SULFIDES

A series of polysubstituted 1,3-dienes were prepared in good overall yields in three steps starting from readily accessible α,α'-diketo sulfides.