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Directing-Group-mediated C-H-Alkynylations.

Lucien D Caspers1, Boris J Nachtsheim1

  • 1Institut für Organische und Analytische Chemie, Universität Bremen, Leobener Straße NW2C, 28359, Bremen, Germany.

Chemistry, an Asian Journal
|March 26, 2018
PubMed
Summary

Directing groups (DGs) enable regioselective metal-catalyzed alkynylation of C-H bonds. This review covers recent advances in DG-mediated C(sp2)-H and C(sp3)-H functionalization with alkynes.

Keywords:
C−C couplingC−H activationalkynescross couplingtransition metals

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Carbon-carbon triple bonds are versatile functional groups in organic synthesis.
  • Direct metal-catalyzed alkynylation of C-H bonds is a rapidly developing field.
  • Regioselectivity in C-H functionalization requires directing groups (DGs) to guide transition metals (TMs).

Purpose of the Study:

  • To review recent developments in directing group-mediated alkynylation of C-H bonds.
  • To discuss modifications involving both C(sp2)-H and C(sp3)-H bonds.
  • To highlight subsequent transformations of the alkyne and directing group.

Main Methods:

  • Focus on DG-mediated C(sp2)-H and C(sp3)-H modifications using terminal alkynes.
  • Discussion of reactions under oxidative conditions and with electrophilic alkynylation reagents.
  • Exploration of alkyne modifications, including cyclizations to carbo- and heterocycles.

Main Results:

  • DG-mediated alkynylation offers a powerful strategy for C-H functionalization.
  • Both C(sp2)-H and C(sp3)-H bonds can be selectively functionalized.
  • Subsequent cyclization reactions enable the synthesis of diverse cyclic compounds.

Conclusions:

  • Directing group strategies are crucial for regioselective C-H alkynylation.
  • This approach provides access to valuable carbo- and heterocycles.
  • Future research can explore further modifications of alkynes and directing groups.