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Synlett 2015; 26(11): 1615-1619
DOI: 10.1055/s-0034-1380714
DOI: 10.1055/s-0034-1380714
letter
Selective and Gram-Scale Synthesis of [6]Cycloparaphenylene
Further Information
Publication History
Received: 12 March 2015
Accepted after revision: 14 April 2015
Publication Date:
20 May 2015 (online)
Dedicated to Professor Peter Vollhardt on the occasion of his 69th birthday
Abstract
A selective, practical, and large-scale synthesis of [6]cycloparaphenylene, the second smallest cycloparaphenylene to be synthesized, was achieved in nine steps starting from commercially available 1,4-dibromobenzene and 4′-bromobiphenyl-4-ol. The key intermediate, cis-1,4-(4-bromophenyl)-1,4-bis(triethylsiloxy)cyclohexa-2,5-diene, was prepared on a large scale (>20 g) and was selectively dimerized to form a cyclic precursor of [6]cycloparaphenylene by platinum-mediated assembly and subsequent reductive elimination. Deprotection of the triethylsilyl group and subsequent tetrachlorostannic acid (H2SnCl4)-mediated reductive aromatization gave [6]cycloparaphenylene in 23% overall yield from the commercially available substrates on gram scale.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380714.
- Supporting Information
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