Direct suzuki-miyaura coupling with naphthalene-1,8-diaminato (dan)-substituted organoborons

Hiroto Yoshida, Michinari Seki, Shintaro Kamio, Hideya Tanaka, Yuki Izumi, Jialun Li, Itaru Osaka, Manabu Abe, Hiroki Andoh, Tomoki Yajima, Tomohiro Tani, Teruhisa Tsuchimoto

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3 Citations (Scopus)

Abstract

The actually direct Suzuki-Miyaura coupling with "protected" R-B(dan) (dan = naphthalene-1,8-diaminato) was demonstrated to smoothly occur without in situ deprotection of the B(dan) moiety. The use of t-BuOK (Ba(OH)2 in some cases) as a base under anhydrous conditions is the key to the successful cross-coupling, where R-B(dan) is readily converted into a transmetalation-active borate-form, regardless of the well-accepted diminished boron-Lewis acidity.

Original languageEnglish
Pages (from-to)346-351
Number of pages6
JournalACS Catalysis
Volume10
Issue number1
DOIs
Publication statusPublished - 3 Jan 2020

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Keywords

  • Boron-Lewis acidity
  • Cross-coupling
  • Direct activation
  • Palladium
  • Protected organoboron

Cite this

Yoshida, H., Seki, M., Kamio, S., Tanaka, H., Izumi, Y., Li, J., Osaka, I., Abe, M., Andoh, H., Yajima, T., Tani, T., & Tsuchimoto, T. (2020). Direct suzuki-miyaura coupling with naphthalene-1,8-diaminato (dan)-substituted organoborons. ACS Catalysis, 10(1), 346-351. https://doi.org/10.1021/acscatal.9b03666