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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
305:
The addition can be done highly regio- and stereoselectively, although the choices of metal, ligands, and counterions often play very important role. Many metals have also been demonstrated to form active catalysts, including nickel and cobalt.
116:
737:
Murai, Shinji; Kakiuchi, Fumitoshi; Sekine, Shinya; Tanaka, Yasuo; Kamatani, Asayuki; Sonoda, Motohiro; Chatani, Naoto (1993-12-09). "Efficient catalytic addition of aromatic carbon-hydrogen bonds to olefins".
816:
Shen, Hong C. (2008). "Recent advances in syntheses of heterocycles and carbocycles via homogeneous gold catalysis. Part 1: Heteroatom addition and hydroarylation reactions of alkynes, allenes, and alkenes".
458:
Ho, C.-Y.; He, L. (2010). "Catalytic
Intermolecular Tail-to-Tail Hydroalkenylation of Styrenes with alpha-Olefins: Regioselective Migratory Insertion Controlled by a Nickel/N-Heterocyclic Carbene".
723:
493:
Ho, C.-Y.; He, L. (2012). "Shuffle Off the
Classic Beta-Si Elimination by Ni-NHC Cooperation: Implication for C–C Forming Reactions Involving Ni-Alkyl-Beta-Silanes".
881:
324:
is again a special case of hydrovinylation. Hydroarylation has been demonstrated for alkyne and alkene substrates. An early example was provided by the
269:{\displaystyle {\ce {PhCH=CH2}}+{\color {red}{\ce {CH2=CH2}}}\longrightarrow {\color {red}{\ce {H -}}}{\ce {CH2-CH(Ph)}}{\color {red}{\ce {-CH=CH2}}}}
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Tony C. T. Chang, Myron
Rosenblum, Nancy Simms (1988). "Vinylation of Enolates with a Vinyl Cation Equivalent: trans-3-Methyl-2-Vinylcyclohexanone".
404:
344:
310:
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Jia, C.; Kitamura, T.; Fujiwara, Y. (2001). "Catalytic
Functionalization of Arenes and Alkanes Via C-H Bond Activation".
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Hilt, G.; Danz, M.; Treutwein, J. (2009). "Cobalt-Catalyzed 1,4-Hydrovinylation of
Styrenes and 1-Aryl-1,3-butadienes".
294:
313:, forming a C-C bond. The resulting metal alkyl undergoes beta-hydride elimination, liberating the vinylated product.
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Li, Yuexuan; Deng, Gongda; Zeng, Xiaoming (2016). "Chromium-Catalyzed
Regioselective Hydropyridination of Styrenes".
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Grutters, M. M. P.; Muller, C.; Vogt, D. (2006). "Highly
Selective Cobalt-Catalyzed Hydrovinylation of Styrene".
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In a stoichiometric version of a hydrovinylation reaction, nucleophiles add to an electrophilic
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The dimerization of ethylene gives 1-butene is another example of a hydrovinylation. In the
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T. V. RajanBabu; G. A. Cox (2014). "5.32 Hydrovinylation
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is a similar reaction, but entails addition of a pyridyl-H bond to alkenes and alkynes.
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Organic reaction which inserts an alkene into a C-H bond of ethylene
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Smith, C. R.; Zhang, A.; Mans, D. J.; Rajanbabu, T. V. (2008).
649:"Asymmetric Hydrovinylation of Unactivated Linear 1,3-Dienes"
423:(2006). "Olefin Metathesis: The Early Days (Nobel Lecture)".
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to give a Pd(II) aryl intermediate. Gold behaves similarly.
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When catalyzed by palladium carboxylates, a key step is
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A Murai reaction (X = directing group, typically X = O).
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Organic Synthesis II (Second Edition)
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106:. A representative reaction is the conversion of
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110:and ethylene to 3-phenybutene:
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102:. The reaction is catalyzed by
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540:: 248–266.
365:vinyl group
74:=CHR + CH
871:Categories
371:References
361:Vinylation
290:Alphabutol
86:−CHR−CH=CH
18:Alphabutol
614:Org. Lett
239:−
216:−
194:−
184:⟶
46:into the
40:insertion
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355:See also
286:Dimersol
52:ethylene
48:C-H bond
877:Alkenes
768:5627826
748:Bibcode
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555:2723857
108:styrene
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740:Nature
704:: 95.
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82:→ CH
44:alkene
42:of an
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511:PMID
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60:C=CH
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669:PMC
661:doi
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622:doi
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78:=CH
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54:(
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