Lewis acid-mediated β-selective hydrocarboxylation of α,α-diaryl- and α-arylalkenes with R3SiH and CO2

Shinya Tanaka, Yuuki Tanaka, Masafumi Chiba, Tetsutaro Hattori

研究成果: Article査読

7 被引用数 (Scopus)

抄録

α,α-Diarylalkenes are successfully hydrocarboxylated with Et3SiH and CO2 with the aid of Et3SiB(C6F5)4 or EtAlCl2/Ph3SiCl to give carboxylic acids with a carboxy group at the β-position to the aryl groups. The EtAlCl2/Ph3SiCl-mediated reaction is also applicable to various α-arylalkenes. 1H NMR analysis of a mixture of EtAlCl2, Ph3SiCl, and Et3SiH strongly suggests the formation of a μ-H complex, [Ph3Si-H-SiEt3]+ AlEtCl3-, which is an equivalent of R3Si+ ions, while Et3SiB(C6F5)4 is an ion pair with a Et3Si+ ion. Therefore, in these reaction systems, a siloxycarbonylium, R3SiOCO+, is considered to be a common electrophile, the addition of which to the substrate, followed by trapping of the resulting cationic species with Et3SiH seems to afford the desired acid after aqueous workup.

本文言語English
ページ(範囲)3830-3834
ページ数5
ジャーナルTetrahedron Letters
56
24
DOI
出版ステータスPublished - 2015 5 30

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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