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Title: Selective and Gram-Scale Synthesis of [6]Cycloparaphenylene
Authors: Kayahara, Eiichi
Patel, Vijay
Xia, Jianlong
Jasti, Ramesh
Yamago, Shigeru  kyouindb  KAKEN_id  orcid (unconfirmed)
Author's alias: 山子, 茂
Keywords: cyclophanes
organometallic reagents
Issue Date: 19-Jun-2015
Publisher: Thieme Publishing Group
Journal title: Synlett
Volume: 26
Issue: 11
Start page: 1615
End page: 1619
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.
Rights: © Georg Thieme Verlag Stuttgart · New York
The full-text file will be made open to the public on 19 June 2016 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
DOI(Published Version): 10.1055/s-0034-1380714
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