56949-84-9

Upstream product

• 588-73-8 (Z)-β-bromostyrene 
• 106-38-7 para-bromotoluene 
• 29541-98-8 pentylidenetriphenylphosphorane 
• 104-87-0 4-methyl-benzaldehyde 
• 109-72-8 n-butyllithium 
• 121758-59-6 (Z,Z)-bis(p-metylstyryl) telluride 
• 60655-80-3 (E)-4-methylstyrenyl bromide 
• 1116-70-7 tri(n-butyl)aluminium 
• 37617-02-0 1-methoxy-1-hexene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 624-31-7 4-tolyl iodide 
• 693-02-7 hex-1-yne 
• 766-97-2 4-n-methylphenylacetylene 

Downstream Products

• 61153-37-5 1-(1E)-1-hexen-1-yl-4-methylbenzene 

Relevant academic research and scientific papers

Copper-NHC-Mediated Semihydrogenation and Hydroboration of Alkynes: Enhanced Catalytic Activity Using Ring-Expanded Carbenes

A series of two-coordinate copper tert-butoxide complexes bearing five-, six-, and seven-membered ring N-heterocyclic carbenes, prepared by protonolysis of (NHC)CuMes with tBuOH, have been used as catalytic precursors in the semihydrogenation of alkynes with silanes/tBuOH and the hydroboration of alkynes with HBPin. Both processes proceed with high regioselectivity and show enhancements with six- and seven-membered ring carbenes.

Metal-Catalyzed Remote Functionalization of ω-Ene Unsaturated Ethers: Towards Functionalized Vinyl Species

The combined ruthenium-catalyzed chain walking with the nickel-catalyzed cross-coupling reaction of ω-alkenyl ethers provide a unique entry to functionalized vinyl species. This transformation illustrates the power and flexibility of remote functionalization by demonstrating the compatibility of two independent reactions involving unrelated sites.

General copper-catalyzed coupling of alkyl-, aryl-, and alkynylaluminum reagents with organohalides

We report the first example of a very general Cu-catalyzed cross-coupling of organoaluminum reagents with organohalides. The reactions proceed for the couplings of alkyl-, aryl-, and alkynylaluminum reagents with aryl and heteroaryl halides and vinyl bromides, affording the cross-coupled products in good to excellent yields. Both primary and secondary alkylaluminum reagents can be utilized as organometallic coupling partners. These reactions are not complicated by β-hydride elimination, and as a result rearranged products are not observed with secondary alkylaluminum reagents even for couplings with heteroaryl halides under "ligand-free" conditions. Radical clock experiment with a radical probe and relative reactivity study of Ph3Al with two haloarenes, 1-bromonaphthalene and 4-chlorobenzonitrile, having two different redox potentials indicates that the reaction does not involve free aryl radicals and radical anions as intermediates. These results combined with the result of the Hammett plot obtained by reacting Ph3Al with iodoarenes containing p-H, p-Me, p-F, and p-CF3 substituents, which shows a linear curve (R2 = 0.99) with a ρ value of +1.06, suggest that the current transformation follows an oxidative addition-reductive elimination pathway.

Highly selective coupling of organoboron compounds via oxovanadium(v)-induced oxidation

Reaction of organoboranes or organoborane ate complexes (obtained by treatment with BunLi or CsF) with oxovanadium(v) compounds results in the intramolecular oxidative coupling of organic groups on the boranes or borates.

Tellurium in organic synthesis. Preparation of Z-vinylic cuprates from Z-vinylic tellurides and their reaction with enones and epoxides

Z-Vinylic tellurides, obtained with 100% stereoselectivity by the hydrotelluration of acetylenes, are easily transformed into Z-vinylic higher order cyanocuprates by reaction with preformed Me2-Cu(CN)Li2, W-Bu2Cu(CN)Lisub

SYNTHESIS OF ALKENES BY WITTIG REACTION USING LITHIUM 1,3-DIAMINOPROPANE AS A BASE

It has been found that the lithium 1,3-diaminopropane (X) can be used for generation of non-stabilized ylides from alkyltriphenylphosphonium salts.These ylides with aldehydes afford olefins in moderate yield with high Z-stereoselectivity.The reaction conditions were studied.