Selective and Gram-Scale Synthesis of [6]Cycloparaphenylene

• Kayahara, Eiichi

• Patel, Vijay

• Xia, Jianlong

• Jasti, Ramesh

• 山子, 茂

抄録

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.

収録刊行物

• Synlett

  Synlett 26 (11), 1615-1619, 2015-06-19

  Thieme Publishing Group

キーワード

• cyclophanes
• cyclizations
• organometallic reagents
• platinum
• tin

詳細情報

• CRID: 1050001335816327168
• NII論文ID: 120005670844
• NII書誌ID: AA10731110
• ISSN: 09365214
• HANDLE: 2433/201542
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles