Ruthenium-Catalyzed Intramolecular Arene C(sp2)-H Amidation for Synthesis of 3,4-Dihydroquinolin-2(1 H)-ones

Wenlong Sun, Cho Hon Ling, Chi Ming Au, Wing Yiu Yu (Corresponding Author)

Research output: Journal article publicationJournal articleAcademic researchpeer-review

Abstract

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

Original languageEnglish
Pages (from-to)3310-3314
Number of pages5
JournalOrganic Letters
Volume23
Issue number9
DOIs
Publication statusPublished - 7 May 2021

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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