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Issue 29, 2014
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Chiral transition-metal complexes as Brønsted-acid catalysts for the asymmetric Friedel–Crafts hydroxyalkylation of indoles

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Abstract

The Friedel–Crafts reaction between 3,3,3-trifluoropyruvates and indoles is efficiently catalysed by the iridium complex [(η5-C5Me5)Ir{(R)-Prophos}(H2O)][SbF6]2 (1) with up to 84% ee. Experimental data and theoretical calculations support a mechanism involving the Brønsted-acid activation of the pyruvate carbonyl by the protons of the coordinated water molecule in 1. Water is not dissociated during the process and, therefore, the catalytic reaction occurs with no direct interaction between the substrates and the metal.

Graphical abstract: Chiral transition-metal complexes as Brønsted-acid catalysts for the asymmetric Friedel–Crafts hydroxyalkylation of indoles

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Publication details

The article was received on 21 Feb 2014, accepted on 11 Apr 2014 and first published on 11 Apr 2014


Article type: Paper
DOI: 10.1039/C4DT00556B
Citation: Dalton Trans., 2014,43, 11260-11268
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    Chiral transition-metal complexes as Brønsted-acid catalysts for the asymmetric Friedel–Crafts hydroxyalkylation of indoles

    D. Carmona, M. P. Lamata, A. Sánchez, F. Viguri, R. Rodríguez, L. A. Oro, C. Liu, S. Díez-González and F. Maseras, Dalton Trans., 2014, 43, 11260
    DOI: 10.1039/C4DT00556B

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