Journal
SYNLETT
Volume 26, Issue 11, Pages 1615-1619Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1380714
Keywords
cyclophanes; cyclizations; organometallic reagents; platinum; tin
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Funding
- CREST Program of the Japan Science and Technology Agency
- [26410043]
- Grants-in-Aid for Scientific Research [26410043] Funding Source: KAKEN
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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.
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