Synthesis of Regioselectively
Functionalized Pyrenes via Transition-Metal-Catalyzed
Electrocyclization

D. Barney Walker; Joshua Howgego; Anthony P. Davis

doi:10.1055/s-0030-1258238

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Synthesis 2010(21): 3686-3692
DOI: 10.1055/s-0030-1258238

PAPER

Synthesis of Regioselectively Functionalized Pyrenes via Transition-Metal-Catalyzed Electrocyclization

D. Barney Walker, Joshua Howgego, Anthony P. Davis*
School of Chemistry, University of Bristol, Cantock’s Close, Bristol, BS8 1TS, UK
Fax: +44(117)9298611; e-Mail: Anthony.Davis@bristol.ac.uk;

Further Information

Publication History

Received 14 July 2010
Publication Date:
01 September 2010 (online)

Abstract
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Abstract

Transition-metal-catalyzed electrocyclic rearrangement of 2,6-diethynyl-1,1′-biphenyl precursors to form polysubstituted pyrenes is described. This method is useful for the preparation of pyrenes with uncommon substitution patterns, and selective integration of functional groups at the 1-, 2-, 3-, 5-, 7- and 9-positions is demonstrated.

Key words

pyrene - electrocyclic reactions - arenes - rearrangements - alkynes

Supporting Information

References

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Supplementary Material

Supporting Information