TY - JOUR
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 (PW12O403-) 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 (PW12O403-) anion. This catalyst was generally more effective and selective toward a broader range of substrates at 70 °C.
UR - http://www.scopus.com/inward/record.url?scp=51749122423&partnerID=8YFLogxK
U2 - 10.1021/ja8051377
DO - 10.1021/ja8051377
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AN - SCOPUS:51749122423
SN - 0002-7863
VL - 130
SP - 11876
EP - 11877
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 36
ER -