20005-88-3

Upstream product

• 1607-57-4 Triphenylvinyl bromide 
• 16419-60-6 2-Methylphenylboronic acid 
• 108-88-3 toluene 
• 591-50-4 iodobenzene 
• 932-31-0 ortho-tolylmagnesium bromide 
• 501-65-5 diphenyl acetylene 
• 615-37-2 ortho-methylphenyl iodide 
• 98-80-6 phenylboronic acid 

Relevant academic research and scientific papers

Synthesis of Tetraarylethene Luminogens by C?H Vinylation of Aromatic Compounds with Triazenes

Tetraarylethenes are obtained by acid-induced coupling of vinyl triazenes with aromatic compounds. This new C?H activation route for the synthesis of aggregation-induced emission luminogens is simple, fast, and versatile. It allows the direct grafting of triarylethenyl groups onto a variety of aromatic compounds, including heterocycles, supramolecular hosts, biologically relevant molecules, and commercial polymers.

Nickel-catalyzed three-component domino reactions of aryl grignard reagents, alkynes, and aryl halides producing tetrasubstituted alkenes

Three-component reaction of aryl Grignard reagents, alkynes, and aryl halides in the presence of 1 mol % of NiCl2 proceeded sequentially through carbomagnesiation of the alkyne followed by cross-coupling of the resulting alkenyl Grignard reagent with aryl halide to give tetrasubstituted alkenes in high yields.

Regio- and stereoselective route to tetrasubstituted olefins by the palladium-catalyzed three-component coupling of aryl iodides, internal alkynes, and arylboronic acids

The Pd-catalyzed three-component coupling of readily available aryl iodides, internal alkynes, and arylboronic acids provides a convenient, one-step, regio- and stereoselective route to tetrasubstituted olefins in good to excellent yields, although electron-poor aryl iodides and dialkylalkynes normally afford only low yields under our standard reaction conditions. The proper combination of substrates and reaction conditions is important for high yields. The presence of water generally substantially increases the yields of the desired tetrasubstituted olefins. The reaction involves cis-addition of the aryl group from the aryl iodide to the less hindered or more electron-rich end of the alkyne, while the aryl group from the arylboronic acid adds to the other end. A modified, room-temperature procedure has also been successfully developed, which works very well for some substrates. Tamoxifen and its derivatives are synthesized in a concise, regio- and stereoselective manner by applying our synthetic protocol.

Synthesis of polysubstituted alkenes by Heck vinylation or Suzuki cross-coupling reactions in the presence of a tetraphosphane-palladium catalyst

Through the use of [PdCl(C3H5)]2/cis,cis,cis-1,2,3, 4-tetrakis[(diphenylphosphanyl)methyl]cyclopentane as a catalyst, a range of vinyl bromides undergo Suzuki cross-couplings with arylboronic acids in good yields. Furthermore, the catalyst can be used at low loadings, even for reactions of sterically hindered substrates. Mediated by this catalyst, stilbene and 1,1-diphenylethylene undergo Heck reactions with aryl halides to give triarylethylene derivatives. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.