95046-18-7

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 201859-33-8 (E)-1-iodo-2-(1-cyclohexenyl)ethene 
• 17962-22-0 1-((trimethylsilyl)ethynyl)cyclohexanol 
• 90598-36-0 <2-(4-Methoxyphenyl)ethenyliden>cyclohexan 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 95046-16-5 1,1-pentamethylene-3-(p-methoxyphenyl)-3-(trimethylsilyl)-1,2-propadiene 

Relevant academic research and scientific papers

Stereospecific Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Cross-Coupling of Aryllithium with Vinyl Halides

We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed.

Synthesis of 1,3-Dienes via a Sequential Suzuki-Miyaura Coupling/Palladium-Mediated Allene Isomerization Sequence

We report a facile method for the synthesis of 1,3-dienes by a sequential process consisting of a palladium-catalyzed, base-free, Suzuki-Miyaura coupling/isomerization sequence. This sequence couples boronic acids with propargyl alcohols, generating the requisite allene in situ, followed by conversion of the unactivated allene to its 1,3-diene via a hydro-palladation/dehydro-palladation process. This process is general for a range of boronic acids, including boronic acids with electron-donating and -withdrawing groups, as well as heteroarylboronic acids. Key to this process is the boric acid byproduct of the base-free Suzuki-Miyauru coupling, which generates the required palladium-hydrido complex [H-PdII-OB(OH)2] required for the isomerization.