Construction of 1,2,3-Benzodiazaborole by Electrophilic Borylation of Azobenzene and Nucleophilic Dialkylative Cyclization

Masanori Shigeno, Masaya Imamatsu, Yusuke Kai, Moe Kiriyama, Shintaro Ishida, Kanako Nozawa-Kumada, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

Abstract

1,2,3-Benzodiazaboroles can be conveniently prepared from azobenzenes by a two-step protocol involving electrophilic ortho-borylation with BBr3 and dialkylative cyclization with the Grignard reagent. The methodology provides a diverse range of products equipped with functionalities from azobenzenes containing substituents (Me, t-Bu, F, Cl, Br, I, and OCF3) and a series of Grignard reagents (alkyl- and arylmagnesium reagents). Moreover, this study displays the moderate aromaticity of the B-N-N-containing five-membered ring and mechanistic investigations of the cyclization reaction.

Original languageEnglish
Pages (from-to)8023-8027
Number of pages5
JournalOrganic letters
Volume23
Issue number20
DOIs
Publication statusPublished - 2021 Oct 15

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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