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

Chen Zhu, J R Falck

Research output: Contribution to journalArticle

43 Scopus citations

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

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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