Synthesis of Benzoisoselenazolone Derivatives by Nickel-Catalyzed Dehydrogenative Direct Selenation of C(sp2)-H Bonds with Elemental Selenium in Air

Masayuki Iwasaki, Natsumi Miki, Yuta Tsuchiya, Kiyohiko Nakajima, Yasushi Nishihara

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Nickel-catalyzed direct selenation of benzamides bearing an 8-quinolyl auxiliary with elemental selenium provides benzoisoselenazolones in good yield via carbon-selenium and nitrogen-selenium bond formation under aerobic conditions. In addition to aryl C-H bonds, the method can also be applied to alkenyl C-H bonds, constructing an isoselenazolone skeleton. Simple mechanistic analysis shows that the reaction proceeds through a rate-determining C-H bond cleavage. The obtained benzoisoselenazolones are transformed into various organoselenium compounds and utilized as the catalyst for bromolactonization of alkenoic acids.

Original languageEnglish
Pages (from-to)1092-1095
Number of pages4
JournalOrganic Letters
Volume19
Issue number5
DOIs
Publication statusPublished - Mar 3 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of Benzoisoselenazolone Derivatives by Nickel-Catalyzed Dehydrogenative Direct Selenation of C(sp<sup>2</sup>)-H Bonds with Elemental Selenium in Air'. Together they form a unique fingerprint.

  • Cite this