2004
DOI: 10.1021/om030605e
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The First Platinum-Catalyzed Hydroamination of Ethylene

Abstract: The platinum-catalyzed hydroamination of ethylene with aniline is reported for the first time. Using PtBr2 as a catalyst precursor in n-Bu4PBr under 25 bar of ethylene pressure affords N-ethylaniline with 80 turnovers after 10 h at 150 °C. The reaction simultaneously produces 2-methylquinoline in ca. 10 cycles. The catalytic activity is slightly improved by increasing the reaction temperature or the ethylene pressure and strongly depends on the aniline/platinum ratio. The beneficial effects of added P(OMe)3 (2… Show more

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Cited by 99 publications
(158 citation statements)
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“…[80] An increase in catalytic efficiency for this solvent was also observed for Rh-catalyzed hydroamination. The platinum system was effective for the high-temperature hydroamination of norbornene, [80] ethylene, [81] and 1-hexene. [82] The selective Markovnikov hydroamination of 1-hexene [Eq.…”
Section: Reviewsmentioning
confidence: 99%
“…[80] An increase in catalytic efficiency for this solvent was also observed for Rh-catalyzed hydroamination. The platinum system was effective for the high-temperature hydroamination of norbornene, [80] ethylene, [81] and 1-hexene. [82] The selective Markovnikov hydroamination of 1-hexene [Eq.…”
Section: Reviewsmentioning
confidence: 99%
“…Besonders gut eignet sich das Platinsystem für die Hydroaminierung von Norbornen, [80] Ethylen [81] und 1-Hexen [82] [87] Platinkatalysatoren sind aber ebenfalls geeignet, wenngleich deutlich geringere Effizienzen resultieren. Matsumoto et al [88,89] [100] In dieser Umsetzung aktiviert das Platin nicht das Alken -wie es bei den meisten in diesem Aufsatz besprochenen Reaktionen der Fall wäre -, sondern das Nucleophil (durch oxidative Addition).…”
Section: Aufsätzeunclassified
“…Brunet and co-workers [12] have shown that molten salts can increase rates and TON values in Rh III -catalyzed (hydroamination of norbornene with anilines) and Pt II -catalyzed reactions (reaction of aniline with ethylene or hexene), giving rise to TON values of up to 250. Moreover, Müller and co-workers [13] described the intramolecular reaction of hex-6-yne-1-amine catalyzed by Lewis acids; conversion and selectivity are improved when the reaction is carried out in ionic liquids.…”
mentioning
confidence: 99%