Issue 54, 2013
From the journal:

Chemical Communications

Ruthenium catalyzed hydroaminoalkylation of isoprenevia transfer hydrogenation: byproduct-free prenylation of hydantoins†

Daniel C. Schmitt,a   Jungyong Lee,a   Anne-Marie R. Dechert-Schmitt,a   Eiji Yamaguchia  and  Michael J. Krische*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, TX 78712, USA
E-mail: mkrische@mail.utexas.edu
Fax: +1 613 9418447
Tel: +1 512 2325892

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.

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

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Article information

DOI
https://doi.org/10.1039/C3CC43463J
Article type
Communication
Submitted
09 May 2013
Accepted
23 May 2013
First published
31 May 2013

Chem. Commun., 2013,49, 6096-6098

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

D. C. Schmitt, J. Lee, A. R. Dechert-Schmitt, E. Yamaguchi and M. J. Krische, Chem. Commun., 2013, 49, 6096 DOI: 10.1039/C3CC43463J

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