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 journalArticle

70 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

Fingerprint

Boranes
boranes
Epoxy Compounds
Manganese
manganese
esters
Esters
Chemical activation
activation
synthesis
Isotopes
Functional groups
Oxygen
isotope effect
Kinetics
Experiments
rings
kinetics
oxygen

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Manganese- and Borane-Mediated Synthesis of Isobenzofuranones from Aromatic Esters and Oxiranes via C-H Bond Activation. / Sueki, Shunsuke; Wang, Zijia; Kuninobu, Yoichiro.

In: Organic Letters, Vol. 18, No. 2, 15.01.2016, p. 304-307.

Research output: Contribution to journalArticle

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