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Angew Chem Int Ed Engl. 2014 Mar 24;53(13):3484-7. doi: 10.1002/anie.201310723. Epub 2014 Feb 19.

Aromatic homologation by non-chelate-assisted Rh(III)-catalyzed C-H functionalization of arenes with alkynes.

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  • 1Laboratory of Asymmetric Catalysis and Synthesis, EPFL SB ISIC LCSA, BCH 4305, 1015 Lausanne (Switzerland) http://isic.epfl.ch/lcsa.

Abstract

Larger condensed arenes are of interest owing to their electro- and photochemical properties. An efficient synthesis is the catalyzed aromatic annulation of a smaller arene with two alkyne molecules. Besides difunctionalized starting materials, directed C-H functionalization can be used for such aromatic homologation. However, thus far the requirement of either pre-functionalized substrates or suitable directing groups were limiting this approach. Herein, we describe a rhodium(III)-catalyzed method allowing the use of completely unbiased arenes and internal alkynes. The reaction works best with copper(II) 2-ethylhexanoate and decabromodiphenyl ether as the oxidant combination. This aromatic annulation tolerates a variety of functional groups and delivers homologated condensed arenes. Aside from simple benzenes, naphthalenes and higher condensed arenes provide access to highly substituted and highly soluble acenes structures having important electronic and photophysical properties.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS:

C-H activation; acenes; alkynes; naphthalenes; rhodium

PMID:
24554591
[PubMed]
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