57044-78-7

Upstream product

• 52812-56-3 (E)-2-ethyl-1-iodohex-1-ene 
• 3220-49-3 phenyl copper 
• 67-56-1 methanol 
• 126979-60-0 3-(triphenylmethyl)heptane 
• 74-85-1 ethene 
• 1129-65-3 (hex-1-yn-1-yl)benzene 
• 1007-32-5 benzyl ethyl ketone 
• 100-59-4 phenylmagnesium chloride 
• 109-72-8 n-butyllithium 
• 622-76-4 1-phenyl-1-butyne 
• 693-03-8 n-butyl magnesium bromide 
• 197139-52-9 trifluoromethanesulfonic acid 1-benzylidenepropyl ester 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 106-35-4 heptan-3-one 

Relevant academic research and scientific papers

Iron-copper cooperative catalysis in the reactions of alkyl grignard reagents: Exchange reaction with alkenes and carbometalation of alkynes

Iron-copper cooperative catalysis is shown to be effective for an alkene-Grignard exchange reaction and alkylmagnesiation of alkynes. The Grignard exchange between terminal alkenes (RCH=CH2) and cyclopentylmagnesium bromide was catalyzed by FeCl3 (2.5 mol %) and CuBr (5 mol %) in combination with PBu3 (10 mol %) to give RCH2CH 2MgBr in high yields. 1-Alkyl Grignard reagents add to alkynes in the presence of a catalyst system consisting of Fe(acac)3, CuBr, PBu3, and N,N,N″,N″-tetramethylethylenediamine to give β-alkylvinyl Grignard reagents. The exchange reaction and carbometalation take place on iron, whereas copper assists with the exchange of organic groups between organoiron and organomagnesium species through transmetalation with these species. Sequential reactions consisting of the alkene-Grignard exchange and the alkylmagnesiation of alkynes were successfully conducted by adding an alkyne to a mixture of the first reaction. Isomerization of Grignard reagents from 2-alkyl to 1-alkyl catalyzed by Fe-Cu also is applicable as the first 1-alkyl Grignard formation step.

Iron-catalyzed carbolithiation of alkynes having no heteroatoms

Alkyl- and aryllithium compounds were found to add to alkynes having no heteroatoms in the presence of an iron or iron-copper catalyst to give various trisubstituted vinyllithium compounds.

Manganese-catalyzed cross-coupling reaction between aryl grignard reagents and alkenyl halides

(Chemical Equation Presented) Aryl Grignard reagents react stereospecifically with alkenyl halides in the presence of manganese chloride (10%) to afford good yields of cross-coupling products.

Selective iron-catalyzed cross-coupling reactions of Grignard reagents with enol triflates, acid chlorides, and dichloroarenes

Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)3 are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the substrates can be selectively monoalkylated by this method. All cross-coupling reactions proceed very rapidly under notably mild conditions and turned out to be compatible with a variety of functional groups in both reaction partners. A detailed analysis of the preparative results suggests that iron-catalyzed C-C bond formations can occur via different pathways. Thus, it is likely that reactions of methylmagnesium halides involve iron-ate complexes as the active components, whereas reactions of Grignard reagents with two or more carbon atoms are effected by highly reduced iron-clusters of the formal composition [Fe(MgX)2]n generated in situ. Control experiments using the ate-complex [Me4Fe]Li2 corroborate this interpretation.

Highly Selective and Practical Alkyne-Alkyne Cross-Coupling Using Cp2ZrBu2 and Ethylene

Highly selective alkyne-alkyne cross coupling reactions were achieved using Cp2ZrBu2 and ethylene gas.First, alkynes were treated with 1.2 equiv of Cp2ZrBu2 (Negishi reagent) under ethylene gas to give zirconacyclopentenes with high selectivities.Subsequent addition of a second alkyne to the solution of zirconacyclopentenes at 50 deg C gave unsymmetrical zirconacyclopentadienes selectively.After hydrolysis unsymmetrical dienes were obtained in high yields.

Photolysis of 1,1,1-Triarylalkane. A New Photochemical Carbene Generation Process

Upon UV irradiation in methanol some 1,1,1-triarylalkanes underwent an α,α-elimination of two aryl groups to give biaryls and the corresponding carbene intermediates, which inserted into the OH bond of the methanol to afford methyl ethers and/or underwent a 1,2-H shift to afford olefins.Furthermore, the efficieny of this elimination was highly dependent upon the bulkiness of the alkyl groups.