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Sequential C-C σ-Bond Cleavage/(sp

Mengdan Wang1, Lingkai Kong1, Ye Wang1

  • 1Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering , East China Normal University , 500 Dongchuan Road , Shanghai 200241 , China.

Organic Letters
|September 15, 2018
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Summary
This summary is machine-generated.

A new synthetic method efficiently creates pyranoindolones using C-C bond cleavage and C-H/O-H coupling. This atom-economical process offers a valuable tool for organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Pyranoindolones are important heterocyclic compounds with diverse biological activities.
  • Developing efficient and atom-economical synthetic routes is crucial for accessing complex molecules.

Purpose of the Study:

  • To develop a novel, atom-economical procedure for synthesizing pyranoindolones fused with medium-sized rings (7- or 8-membered).
  • To explore a sequential reaction involving C-C sigma-bond cleavage and C-H/O-H coupling.

Main Methods:

  • Utilized a sequential reaction strategy.
  • Employed cesium carbonate (Cs2CO3) for C-C sigma-bond cleavage of cyclic ketoesters.
  • Applied zinc iodide (ZnI2) for selective C-H/O-H coupling.

Main Results:

  • Successfully synthesized pyranoindolones fused with 7- or 8-membered rings.
  • Achieved cleavage of two C-C sigma-bonds and functionalization of an sp2 C-H bond in a single process.
  • Demonstrated the utility of easily accessible starting materials and a broad substrate scope.

Conclusions:

  • The developed protocol is atom-economical and efficient for constructing fused pyranoindolone systems.
  • The method offers a versatile and attractive approach for synthetic organic chemists.
  • Highlights the potential of combining C-C bond cleavage with C-H functionalization in heterocyclic synthesis.