65663-77-6

Upstream product

• 111-66-0 oct-1-ene 
• 95-46-5 2-methylphenyl bromide 
• 16419-60-6 2-Methylphenylboronic acid 
• 52356-93-1 (Z)-1-octenyl iodide 
• 932-31-0 ortho-tolylmagnesium bromide 
• 51751-87-2 (E)-1-bromo-1-octene 
• 106-38-7 para-bromotoluene 
• 42599-17-7 (E)-1-iodo-1-octene 
• 853955-61-0 (E)-[2-(hydroxymethyl)phenyl]-dimethyl-(1-octenyl)-silane 
• 615-37-2 ortho-methylphenyl iodide 
• 108-88-3 toluene 

Relevant academic research and scientific papers

Improved procedure for single-electron-transfer-induced grignard cross-coupling reaction

Aryl Grignard reagents were found to undergo coupling with aryl or alkenyl bromides in the presence of LiCl in a mixed solvent consisting of toluene and THF (2/1). Previously employed removal of THF with evacuation from Grignard solutions is no longer needed to obtain biaryls and styrene derivatives.

Single electron transfer-induced cross-coupling reaction of alkenyl halides with aryl Grignard reagents

Alkenyl halides were found to undergo coupling with aryl Grignard reagents to give the corresponding styrene derivatives in a stereo-retained manner. The cross-coupling reaction is considered to proceed through a single electron transfer mechanism.

Ligand effects on the stereochemical outcome of suzuki-miyaura couplings

The ligands associated with various Pd catalysts play a crucial role in determining the stereochemistry of cross-couplings between boronic acids and Z-alkenyl halides. A ligand on palladium has been found that leads to the desired products under mild conditions and in high yields that, in most cases, retain their Z-olefin geometry.

Silicon-Based Cross-Coupling Reagent and Production Method of Organic Compound Using the Same

In one embodiment of the present invention, a silicon-based cross-coupling reagent is disclosed which is a highly stable tetraorganosilicon compound allowing for a cross-coupling reaction under mild reaction conditions without using fluoride ions, transition metal promoter, or strong bases, and the residue of the silicon reagent can be recovered and reused. The silicon-based cross-coupling reagent is a silicon compound in which an o-hydroxymethylphenyl group is connected to a silicon atom for intramolecular activation.

Palladium-tetraphosphine catalysed heck reaction with simple alkenes: Influence of reaction conditions on the migration of the double bond

The Heck reaction of aryl halides with simple alk-1-enes is a powerful method for the synthesis of (E)-1-arylalk-1-ene derivatives. The major problem of this reaction is the palladium-catalysed migration of the carbon-carbon double bond along the alkyl ch

Synthesis and cross-coupling reaction of alkenyl[(2-hydroxymethyl)phenyl]dimethylsilanes

Highly stable alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes are prepared by stereo- and regioselective hydrosilylation of alkynes catalyzed either by a platinum or ruthenium catalyst using protected [2-(hydroxymethyl)phenyl]dimethylsilanes. Cyclic silyl ether, 1,1-dimethyl-2-oxa-1-silaindan, also serves as a starting material for the alkenylsilanes by the ring-opening reaction with alkenyl Grignard reagents. The resulting alkenylsilanes undergo cross-coupling reaction with various aryl and alkenyl iodides under reaction conditions employing K2CO3 as a base at 35-50 °C in highly regio- and stereospecific manners. The reaction tolerates a diverse range of functional groups including silyl protections. The silicon residue is readily recovered and reused on a gram-scale synthesis. Intramolecular coordination of a proximal hydroxyl group is considered to efficiently form pentacoordinate silicates having a transferable group possibly at an axial position and, thus, responsible for the cross-coupling reaction under conditions significantly milder than those reported for the silicon-based reactions.

Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes: An entry to tetraorganosilicon reagents for the silicon-based cross-coupling reaction

Alkenyl- and aryl[2-(hydroxymethyl)phenyl]dimethylsilanes, highly stable tetraorganosilicon reagents, are found to react with aryl and alkenyl iodides in the presence of a palladium catalyst and K2CO3 as a base, significantly milder conditions compared with those ever reported for the silicon-based cross-coupling reactions. The reaction tolerates a wide range of functional groups, including silyl protectors, and allows a gram-scale synthesis to recover and reuse the silicon residue. Copyright