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When catalyzed by palladium carboxylates, a key step is electrophilic aromatic substitution to give a Pd(II) aryl intermediate. Gold behaves similarly. Hydropyridination is a similar reaction, but entails addition of a pyridyl-H bond to alkenes and alkynes.
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; ...
, hydrovinylation is the formal insertion
Insertion may refer to:
*Insertion (anatomy), the point of a tendon or ligament onto the skeleton or other part of the body
*Insertion (genetics), the addition of DNA into a genetic sequence
*Insertion, several meanings in medicine, see ICD-10-PCS
...
of an alkene
In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.
Alkene is often used as synonym of olefin, that is, any hydrocarbon containing one or more double bonds.H. Stephen Stoker (2015): General, Organic, an ...
into the C-H bond of ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds).
Ethylene i ...
(). The more general reaction, hydroalkenylation, is the formal insertion of an alkene into the C-H bond of any terminal alkene. The reaction is catalyzed by metal complexes. A representative reaction is the conversion of styrene and ethylene to 3-phenybutene:
:
Ethylene dimerization
The dimerization of ethylene gives 1-butene is another example of a hydrovinylation. In the Dimersol and Alphabutol Processes, alkenes are dimerized for the production of gasoline and for comonomers such as 1-butene. These processes operate at several refineries across the world at the scales of about 400,000 tons/year (2006 report). 1-Butene is amenable to isomerization to 2-butenes, which is used in Olefin conversion technology to give propylene.Hydroarylation
Hydroarylation is again a special case of hydrovinylation. Hydroarylation has been demonstrated for alkyne and alkene substrates. An early example was provided by the Murai reaction, which involves the insertion of alkenes into a C-H bond of acetophenone. The keto group directs the regiochemistry, stabilizing an aryl intermediate.
When catalyzed by palladium carboxylates, a key step is electrophilic aromatic substitution to give a Pd(II) aryl intermediate. Gold behaves similarly. Hydropyridination is a similar reaction, but entails addition of a pyridyl-H bond to alkenes and alkynes.
In organic synthesis
As first reported by Alderson, Jenner and Lindsey, hydrovinylation uses rhodium- and ruthenium-based catalysts. Catalysts based on iron, cobalt, nickel, and palladium have also been demonstrated. The addition can be done highly regio- and stereoselectively, the choices of metal centers, ligands, substrates and counterions often play very important role. N-heterocyclic carbene complexes of Ni allow the selective preparations of functionalized geminal olefins or 1,1-disubstituted alkenes.{{cite journal , author = Ho, C.-Y. , author2=He, L. , year = 2012 , pages = 1481–1483 , title = Shuffle Off the Classic Beta-Si Elimination by Ni-NHC Cooperation: Implication for C–C Forming Reactions Involving Ni-Alkyl-Beta-Silanes , issue = 10 , pmid = 22116100 , journal = Chem. Commun. , volume = 48 , doi = 10.1039/c1cc14593bReferences