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Ruthenium catalyzed hydroaminoalkylation of isoprene via transfer hydrogenation: byproduct-free prenylation of hydantoins.

ABSTRACT: The ruthenium catalyst derived from Ru3(CO)12 and triphos [Ph2P(CH2CH2PPh2)2] promotes the direct C-C coupling of isoprene with aryl substituted hydantoins 1a–1f at the diene C4-position to furnish products of n-prenylation 2a–2f. A mechanism involving hydantoin dehydrogenation followed by diene-imine oxidative coupling to furnish a transient aza-ruthencyclopentene is proposed.

SUBMITTER: Schmitt DC

PROVIDER: S-EPMC3730527 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Ruthenium catalyzed hydroaminoalkylation of isoprene via transfer hydrogenation: byproduct-free prenylation of hydantoins.

Schmitt Daniel C DC Lee Jungyong J Dechert-Schmitt Anne-Marie R AM Yamaguchi Eiji E Krische Michael J MJ

Chemical communications (Cambridge, England) 20130701 54

The ruthenium catalyst derived from Ru3(CO)12 and triphos [Ph2P(CH2CH2PPh2)2] promotes the direct C-C coupling of isoprene with aryl substituted hydantoins 1a–1f at the diene C4-position to furnish products of n-prenylation 2a–2f. A mechanism involving hydantoin dehydrogenation followed by diene-imine oxidative coupling to furnish a transient aza-ruthencyclopentene is proposed. ...[more]

PMID: 23722271

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