Copper-catalyzed reactions for organic synthesis

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Editors: Gwilherm Evano, Université libre de Bruxelles, and
Olivier Riant, Université Catholique de Louvain
 

Catalysis with transition metal complexes occupies a central place in organic synthesis and has enabled the development of a number of remarkably efficient reactions. Among all transition metals, copper has proven to be one of the most versatile one. In addition to its abundancy and its low cost, copper can accommodate a wide variety of ligands and its accessible oxidation states ranging from 0 to III allow the catalysis of a broad range of processes. They notably include cross-coupling reactions for the formation of carbon–carbon and carbon–heteroatom bonds, (enantioselective) additions to multiple bonds and nucleophilic substitutions, radical processes, selective oxidations, cyclopropanations, cycloadditions, aziridinations... The unique coordination and inorganic properties of copper complexes are in addition also central to their use as chiral Lewis acids or photoredox catalysts.

Most of these copper-catalyzed reactions are commonly utilized both in academia and industry: they are at the core of this thematic issue that will highlight the key role played by copper catalysis in contemporary organic synthesis.

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Synthesis of aryl cyclopropyl sulfides through copper-promoted S-cyclopropylation of thiophenols using cyclopropylboronic acid

  • Emeline Benoit,
  • Ahmed Fnaiche and
  • Alexandre Gagnon

Beilstein J. Org. Chem. 2019, 15, 1162–1171, doi:10.3762/bjoc.15.113

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Published 27 May 2019

Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones

  • Riccardo Innocenti,
  • Elena Lenci,
  • Gloria Menchi and
  • Andrea Trabocchi

Beilstein J. Org. Chem. 2020, 16, 200–211, doi:10.3762/bjoc.16.23

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Published 12 Feb 2020

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

  • Delphine Pichon,
  • Jennifer Morvan,
  • Christophe Crévisy and
  • Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

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Published 17 Feb 2020

Copper-promoted/copper-catalyzed trifluoromethylselenolation reactions

  • Clément Ghiazza and
  • Anis Tlili

Beilstein J. Org. Chem. 2020, 16, 305–316, doi:10.3762/bjoc.16.30

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Published 03 Mar 2020

Recent advances in photocatalyzed reactions using well-defined copper(I) complexes

  • Mingbing Zhong,
  • Xavier Pannecoucke,
  • Philippe Jubault and
  • Thomas Poisson

Beilstein J. Org. Chem. 2020, 16, 451–481, doi:10.3762/bjoc.16.42

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Published 23 Mar 2020

Aerobic synthesis of N-sulfonylamidines mediated by N-heterocyclic carbene copper(I) catalysts

  • Faïma Lazreg,
  • Marie Vasseur,
  • Alexandra M. Z. Slawin and
  • Catherine S. J. Cazin

Beilstein J. Org. Chem. 2020, 16, 482–491, doi:10.3762/bjoc.16.43

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Published 24 Mar 2020

Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary carbons

  • Goki Hirata,
  • Yu Yamane,
  • Naoya Tsubaki,
  • Reina Hara and
  • Takashi Nishikata

Beilstein J. Org. Chem. 2020, 16, 502–508, doi:10.3762/bjoc.16.45

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Published 26 Mar 2020

Copper-catalyzed O-alkenylation of phosphonates

  • Nuria Vázquez-Galiñanes,
  • Mariña Andón-Rodríguez,
  • Patricia Gómez-Roibás and
  • Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2020, 16, 611–615, doi:10.3762/bjoc.16.56

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Published 03 Apr 2020

Recent advances in Cu-catalyzed C(sp3)–Si and C(sp3)–B bond formation

  • Balaram S. Takale,
  • Ruchita R. Thakore,
  • Elham Etemadi-Davan and
  • Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

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Published 15 Apr 2020

Copper catalysis with redox-active ligands

  • Agnideep Das,
  • Yufeng Ren,
  • Cheriehan Hessin and
  • Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

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Published 24 Apr 2020

Copper-catalysed alkylation of heterocyclic acceptors with organometallic reagents

  • Yafei Guo and
  • Syuzanna R. Harutyunyan

Beilstein J. Org. Chem. 2020, 16, 1006–1021, doi:10.3762/bjoc.16.90

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Published 14 May 2020

Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F)

  • Louise Ruyet and
  • Tatiana Besset

Beilstein J. Org. Chem. 2020, 16, 1051–1065, doi:10.3762/bjoc.16.92

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Published 18 May 2020
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