Manganese- and Borane-Mediated Synthesis of Isobenzofuranones from Aromatic Esters and Oxiranes via C-H Bond Activation

Shunsuke Sueki, Zijia Wang, Yoichiro Kuninobu

Research output: Contribution to journalArticlepeer-review

77 Citations (Scopus)

Abstract

A manganese- and borane-mediated synthesis of isobenzofuranones from esters and oxiranes is developed. The reaction proceeded at aromatic, heteroaromatic, and olefinic C-H bonds with high functional group tolerance. This is the first example of a manganese-catalyzed C-H transformation using an oxygen-directing group. Triphenylborane played an important role in this reaction to cooperatively promote the annulation reaction. Kinetic isotope effect experiments revealed that C-H bond activation of the aromatic rings was the rate-determining step.

Original languageEnglish
Pages (from-to)304-307
Number of pages4
JournalOrganic Letters
Volume18
Issue number2
DOIs
Publication statusPublished - Jan 15 2016
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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