Issue 23, 2015
From the journal:

Chemical Communications

Unprecedented pseudo-ortho and ortho metallation of [2.2]paracyclophanes – a methyl group matters†

Mirja Enders,a   Christian J. Friedmann,a   Philipp N. Plessow,b   Angela Bihlmeier,b   Martin Nieger,c   Wim Klopperb  and  Stefan Bräse*ad  

* Corresponding authors

a Institute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
E-mail: braese@kit.edu

b Institute of Physical Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 2, 76131 Karlsruhe, Germany
E-mail: klopper@kit.edu

c Laboratory of Inorganic Chemistry, University of Helsinki, P. O. Box 55, Finland
E-mail: martin.nieger@helsinki.fi

d Institute of Toxicology and Genetics, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen, Germany

Abstract

The first example of a pseudo-ortho metallation on [2.2]paracyclophane is presented, giving easy access to enantiopure compounds of this type. By slight modification of the directing group, metallation of the ortho- and C2-positions is possible. The mechanism was further investigated by means of density functional theory (DFT) calculations.

Graphical abstract: Unprecedented pseudo-ortho and ortho metallation of [2.2]paracyclophanes – a methyl group matters

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Article information

DOI
https://doi.org/10.1039/C5CC00492F
Article type
Communication
Submitted
18 Jan 2015
Accepted
10 Feb 2015
First published
10 Feb 2015

Chem. Commun., 2015,51, 4793-4795

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Unprecedented pseudo-ortho and ortho metallation of [2.2]paracyclophanes – a methyl group matters

M. Enders, C. J. Friedmann, P. N. Plessow, A. Bihlmeier, M. Nieger, W. Klopper and S. Bräse, Chem. Commun., 2015, 51, 4793 DOI: 10.1039/C5CC00492F

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