|Title:||Selective and Gram-Scale Synthesis of Cycloparaphenylene|
Yamago, Shigeru https://orcid.org/0000-0002-4112-7249 (unconfirmed)
|Author's alias:||山子, 茂|
|Publisher:||Thieme Publishing Group|
|Abstract:||A selective, practical, and large-scale synthesis of 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 cycloparaphenylene by platinum-mediated assembly and subsequent reductive elimination. Deprotection of the triethylsilyl group and subsequent tetrachlorostannic acid (H2SnCl4)-mediated reductive aromatization gave cycloparaphenylene in 23% overall yield from the commercially available substrates on gram scale.|
|Rights:||© Georg Thieme Verlag Stuttgart · New York|
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|Appears in Collections:||Journal Articles|
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