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Rollover-assisted C(sp2)-C(sp3) bond formation.

Antonio Zucca1, Luca Maidich, Laura Canu

  • 1Dipartimento di Chimica e Farmacia, Università degli Studi di Sassari, Via Vienna 2, 07100 Sassari (Italy). zucca@uniss.it.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 1, 2014
PubMed
Summary
This summary is machine-generated.

This study introduces rollover cyclometalation, a novel platinum-catalyzed reaction. It achieves rare C(sp2)-C(sp3) bond formation, enabling new C-H functionalization of heterocyclic compounds.

Keywords:
NMR spectroscopybond couplingplatinumreductive eliminationrollover cyclometalation

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Rollover cyclometalation is a unique reaction involving bidentate heterocyclic donors.
  • Classical cyclometalated complexes exhibit different reactivity compared to products with free donor atoms.

Purpose of the Study:

  • To explore the
  • rollover
  • /
  • "retro-rollover"
  • reaction sequence in platinum(II) complexes.
  • To develop a new method for C-H bond activation and functionalization at the C(3) position of bidentate heterocyclic compounds.

Main Methods:

  • Utilized a series of platinum(II) complexes [Pt(N,C)(Me)(PR3)].
  • Employed a sequence of oxidative addition and reductive elimination reactions.
  • Isolated and characterized the resulting bidentate nitrogen ligands.

Main Results:

  • Achieved a rare C(sp2)-C(sp3) bond formation.
  • Synthesized 3-methyl-2,2'-bipyridine, 3,6-dimethyl-2,2'-bipyridine, and 3-methyl-2-(2'-pyridyl)-quinoline.
  • Demonstrated that the nature of the phosphane ligand (PR3) is crucial for reaction outcome.

Conclusions:

  • The developed route provides a novel method for functionalizing the typically inert C(3) position of bidentate heterocycles.
  • This work expands the synthetic utility of rollover cyclometalation in organometallic chemistry.