Rhodium catalyzed synthesis of isoindolinones via C-H activation of N-benzoylsulfonamides

Chen Zhu, J R Falck

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

An efficient approach to a wide range of isoindolinones, including 3-monosubstituted and 3,3-disubstituted isoindolinones, from the annulation of N-benzoylsulfonamides with olefins and diazoacetate has been developed. The transformation is broadly compatible with both terminal and internal olefins. Moreover, diazoacetate is for the first time incorporated into an amide-directed C-H functionalization reaction. Specifically, the rhodium complex [{RhCl 2Cp*} 2] enables the in situ dimerization of diazoacetate in addition to its role in catalyzing C-H functionalization/cross- coupling.

Original languageEnglish (US)
Pages (from-to)9192-9199
Number of pages8
JournalTetrahedron
Volume68
Issue number45
DOIs
StatePublished - Nov 11 2012

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Rhodium
Alkenes
Chemical activation
Dimerization
Amides

Keywords

  • C-H activation
  • Diazoacetate
  • Isoindolinone
  • N-Benzoylsulfonamide
  • Rhodium catalysis

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Rhodium catalyzed synthesis of isoindolinones via C-H activation of N-benzoylsulfonamides. / Zhu, Chen; Falck, J R.

In: Tetrahedron, Vol. 68, No. 45, 11.11.2012, p. 9192-9199.

Research output: Contribution to journalArticle

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