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Synthesis 2004(18): 3084-3088  
DOI: 10.1055/s-2004-834894
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© Georg Thieme Verlag Stuttgart · New York

Selective [2+2+2] Cycloaddition of Nickel-Benzyne and an Asymmetric 1,3-Diyne: An Iterative Route to Substituted [n]Acenes

Kimberly R. Deaton, Christopher S. Strouse, Mary S. Gin*
Department of Chemistry, University of Illinois at Urbana-Champaign, 600 S. Mathews Ave, Urbana, IL 61801, USA
Fax: +1(217)2448024; e-Mail: mgin@scs.uiuc.edu;
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Publication History

Received 4 September 2004
Publication Date:
22 October 2004 (online)

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Abstract

A new iterative route to substituted acenes is reported that centers on regioselective cycloaddition of a nickel-benzyne and 1-trimethylsilyl-1,3-pentadiyne. The five-step sequence installs two fused aromatic rings and two methyl substituents onto the backbone in 27% overall yield.

Key words

alkynes - cycloaddition - fused-ring systems - nickel - regioselectivity