Nitrosonium salts, NO+X- (X = B(3,5-diCF 3Ph)4 - or PW12O40 3-), as electrophilic catalysts for alkene activation in arene alkylation and dimerization reactions

Alexander M. Khenkin, Ronny Neumann

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26 Citations (Scopus)

Abstract

It has been found that in apolar reaction media the nitrosonium cation (NO+) activated alkenes under mild conditions toward electrophilic substitution of arene substrates to yield the alkylated arene with Markovnikov orientation. In the absence of arenes the alkenes react with themselves to yield a mixture of dimeric alkenes. The nitrosonium cation can be dissolved in the reaction medium by using the tetrakis-(bis-(3,5-trifluromethyl)phenyl) borate anion, where upon the reactions occur effectively at 30 °C. Alternatively an insoluble, heterogeneous catalyst was prepared so as to yield a NO+ cation with a polyoxometalate (PW12O40 3-) anion. This catalyst was generally more effective and selective toward a broader range of substrates at 70 °C.

Original languageEnglish
Pages (from-to)11876-11877
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number36
DOIs
Publication statusPublished - Sep 10 2008

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Dimerization
Alkylation
Alkenes
Olefins
Cations
Salts
Positive ions
Chemical activation
Catalysts
Anions
Negative ions
Borates
Substrates
Substitution reactions

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Nitrosonium salts, NO+X- (X = B(3,5-diCF 3Ph)4 - or PW12O40 3-), as electrophilic catalysts for alkene activation in arene alkylation and dimerization reactions",
abstract = "It has been found that in apolar reaction media the nitrosonium cation (NO+) activated alkenes under mild conditions toward electrophilic substitution of arene substrates to yield the alkylated arene with Markovnikov orientation. In the absence of arenes the alkenes react with themselves to yield a mixture of dimeric alkenes. The nitrosonium cation can be dissolved in the reaction medium by using the tetrakis-(bis-(3,5-trifluromethyl)phenyl) borate anion, where upon the reactions occur effectively at 30 °C. Alternatively an insoluble, heterogeneous catalyst was prepared so as to yield a NO+ cation with a polyoxometalate (PW12O40 3-) anion. This catalyst was generally more effective and selective toward a broader range of substrates at 70 °C.",
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T1 - Nitrosonium salts, NO+X- (X = B(3,5-diCF 3Ph)4 - or PW12O40 3-), as electrophilic catalysts for alkene activation in arene alkylation and dimerization reactions

AU - Khenkin, Alexander M.

AU - Neumann, Ronny

PY - 2008/9/10

Y1 - 2008/9/10

N2 - It has been found that in apolar reaction media the nitrosonium cation (NO+) activated alkenes under mild conditions toward electrophilic substitution of arene substrates to yield the alkylated arene with Markovnikov orientation. In the absence of arenes the alkenes react with themselves to yield a mixture of dimeric alkenes. The nitrosonium cation can be dissolved in the reaction medium by using the tetrakis-(bis-(3,5-trifluromethyl)phenyl) borate anion, where upon the reactions occur effectively at 30 °C. Alternatively an insoluble, heterogeneous catalyst was prepared so as to yield a NO+ cation with a polyoxometalate (PW12O40 3-) anion. This catalyst was generally more effective and selective toward a broader range of substrates at 70 °C.

AB - It has been found that in apolar reaction media the nitrosonium cation (NO+) activated alkenes under mild conditions toward electrophilic substitution of arene substrates to yield the alkylated arene with Markovnikov orientation. In the absence of arenes the alkenes react with themselves to yield a mixture of dimeric alkenes. The nitrosonium cation can be dissolved in the reaction medium by using the tetrakis-(bis-(3,5-trifluromethyl)phenyl) borate anion, where upon the reactions occur effectively at 30 °C. Alternatively an insoluble, heterogeneous catalyst was prepared so as to yield a NO+ cation with a polyoxometalate (PW12O40 3-) anion. This catalyst was generally more effective and selective toward a broader range of substrates at 70 °C.

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