Copper catalysis in organic synthesis

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Editor: Prof. Sherry R. Chemler
University at Buffalo
 
The growth in copper-catalyzed organic reactions is driven by a couple of factors. First, copper chemistry is incredibly diverse. Depending on its oxidation state, this metal can efficiently catalyze reactions involving both one and two-electron mechanisms. Copper coordinates easily to heteroatoms and to π-bonds and is well-known to activate terminal alkynes. The Ullman and Goldberg C–C and C–N cross-coupling reactions were discovered over a century ago and their development has really blossomed over the past twenty years. Second, copper is an earth-abundant metal, making its use more cost effective and more sustainable than precious transition metal catalysts. It is clear from the impact copper catalysis has had on organic synthesis that copper should be considered a first line catalyst for many organic reactions. Further growth in the field is anticipated in the years to come.

See also the Thematic Series:
Transition-metal and organocatalysis in natural product synthesis
Gold catalysis for organic synthesis II

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Copper catalysis in organic synthesis

  • Sherry R. Chemler

Beilstein J. Org. Chem. 2015, 11, 2252–2253, doi:10.3762/bjoc.11.244

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Published 19 Nov 2015

Synthesis of alpha-tetrasubstituted triazoles by copper-catalyzed silyl deprotection/azide cycloaddition

  • Zachary L. Palchak,
  • Paula T. Nguyen and
  • Catharine H. Larsen

Beilstein J. Org. Chem. 2015, 11, 1425–1433, doi:10.3762/bjoc.11.154

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Published 14 Aug 2015

Copper-catalyzed aerobic radical C–C bond cleavage of N–H ketimines

  • Ya Lin Tnay,
  • Gim Yean Ang and
  • Shunsuke Chiba

Beilstein J. Org. Chem. 2015, 11, 1933–1943, doi:10.3762/bjoc.11.209

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Published 19 Oct 2015

Effective ascorbate-free and photolatent click reactions in water using a photoreducible copper(II)-ethylenediamine precatalyst

  • Redouane Beniazza,
  • Natalia Bayo,
  • Florian Molton,
  • Carole Duboc,
  • Stéphane Massip,
  • Nathan McClenaghan,
  • Dominique Lastécouères and
  • Jean-Marc Vincent

Beilstein J. Org. Chem. 2015, 11, 1950–1959, doi:10.3762/bjoc.11.211

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Published 21 Oct 2015

Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water

  • Lei Zhu,
  • Taku Kitanosono,
  • Pengyu Xu and
  • Shū Kobayashi

Beilstein J. Org. Chem. 2015, 11, 2007–2011, doi:10.3762/bjoc.11.217

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Published 27 Oct 2015

A new approach to ferrocene derived alkenes via copper-catalyzed olefination

  • Vasily M. Muzalevskiy,
  • Aleksei V. Shastin,
  • Alexandra D. Demidovich,
  • Namiq G. Shikhaliev,
  • Abel M. Magerramov,
  • Victor N. Khrustalev,
  • Rustem D. Rakhimov,
  • Sergey Z. Vatsadze and
  • Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2015, 11, 2072–2078, doi:10.3762/bjoc.11.223

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Published 03 Nov 2015

Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines

  • Dimitra Kontokosta,
  • Daniel S. Mueller,
  • Dong-Liang Mo,
  • Wiktoria H. Pace,
  • Rachel A. Simpson and
  • Laura L. Anderson

Beilstein J. Org. Chem. 2015, 11, 2097–2104, doi:10.3762/bjoc.11.226

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Published 04 Nov 2015

C–H bond halogenation catalyzed or mediated by copper: an overview

  • Wenyan Hao and
  • Yunyun Liu

Beilstein J. Org. Chem. 2015, 11, 2132–2144, doi:10.3762/bjoc.11.230

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Published 09 Nov 2015

Coupling of α,α-difluoro-substituted organozinc reagents with 1-bromoalkynes

  • Artem A. Zemtsov,
  • Alexander D. Volodin,
  • Vitalij V. Levin,
  • Marina I. Struchkova and
  • Alexander D. Dilman

Beilstein J. Org. Chem. 2015, 11, 2145–2149, doi:10.3762/bjoc.11.231

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Published 10 Nov 2015

Molecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles

  • Wen Ding,
  • Shaoyu Mai and
  • Qiuling Song

Beilstein J. Org. Chem. 2015, 11, 2158–2165, doi:10.3762/bjoc.11.233

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Published 11 Nov 2015

Recent advances in copper-catalyzed C–H bond amidation

  • Jie-Ping Wan and
  • Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

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Published 17 Nov 2015

Recent developments in copper-catalyzed radical alkylations of electron-rich π-systems

  • Kirk W. Shimkin and
  • Donald A. Watson

Beilstein J. Org. Chem. 2015, 11, 2278–2288, doi:10.3762/bjoc.11.248

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Published 23 Nov 2015

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

  • Svetlana P. Panchenko,
  • Alexei D. Averin,
  • Maksim V. Anokhin,
  • Olga A. Maloshitskaya and
  • Irina P. Beletskaya

Beilstein J. Org. Chem. 2015, 11, 2297–2305, doi:10.3762/bjoc.11.250

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Published 24 Nov 2015

A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations

  • Xinlong Pang,
  • Chao Chen,
  • Ming Li and
  • Chanjuan Xi

Beilstein J. Org. Chem. 2015, 11, 2365–2369, doi:10.3762/bjoc.11.258

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Published 30 Nov 2015

Copper-catalyzed arylation of alkyl halides with arylaluminum reagents

  • Bijay Shrestha and
  • Ramesh Giri

Beilstein J. Org. Chem. 2015, 11, 2400–2407, doi:10.3762/bjoc.11.261

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Published 02 Dec 2015

Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

  • Thibault E. Schmid,
  • Sammy Drissi-Amraoui,
  • Christophe Crévisy,
  • Olivier Baslé and
  • Marc Mauduit

Beilstein J. Org. Chem. 2015, 11, 2418–2434, doi:10.3762/bjoc.11.263

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Published 03 Dec 2015

Copper-catalysed asymmetric allylic alkylation of alkylzirconocenes to racemic 3,6-dihydro-2H-pyrans

  • Emeline Rideau and
  • Stephen P. Fletcher

Beilstein J. Org. Chem. 2015, 11, 2435–2443, doi:10.3762/bjoc.11.264

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Published 03 Dec 2015

Copper-catalyzed stereoselective conjugate addition of alkylboranes to alkynoates

  • Takamichi Wakamatsu,
  • Kazunori Nagao,
  • Hirohisa Ohmiya and
  • Masaya Sawamura

Beilstein J. Org. Chem. 2015, 11, 2444–2450, doi:10.3762/bjoc.11.265

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Published 04 Dec 2015

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

  • Zhan-Jiang Zheng,
  • Ding Wang,
  • Zheng Xu and
  • Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

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Published 11 Dec 2015

Recent advances in copper-catalyzed asymmetric coupling reactions

  • Fengtao Zhou and
  • Qian Cai

Beilstein J. Org. Chem. 2015, 11, 2600–2615, doi:10.3762/bjoc.11.280

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Published 15 Dec 2015

Carbon–carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations

  • Tsuyuka Sugiishi,
  • Hideki Amii,
  • Kohsuke Aikawa and
  • Koichi Mikami

Beilstein J. Org. Chem. 2015, 11, 2661–2670, doi:10.3762/bjoc.11.286

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Published 18 Dec 2015

Enantioselective additions of copper acetylides to cyclic iminium and oxocarbenium ions

  • Jixin Liu,
  • Srimoyee Dasgupta and
  • Mary P. Watson

Beilstein J. Org. Chem. 2015, 11, 2696–2706, doi:10.3762/bjoc.11.290

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Published 22 Dec 2015

Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives

  • Yan Li,
  • Xue Zhou,
  • Guangfan Zheng and
  • Qian Zhang

Beilstein J. Org. Chem. 2015, 11, 2721–2726, doi:10.3762/bjoc.11.293

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Published 24 Dec 2015

Copper-catalyzed intermolecular oxyamination of olefins using carboxylic acids and O-benzoylhydroxylamines

  • Brett N. Hemric and
  • Qiu Wang

Beilstein J. Org. Chem. 2016, 12, 22–28, doi:10.3762/bjoc.12.4

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Published 07 Jan 2016

Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes

  • H. Surya Prakash Rao and
  • A. Veera Bhadra Rao

Beilstein J. Org. Chem. 2016, 12, 496–504, doi:10.3762/bjoc.12.49

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Published 11 Mar 2016

Studies on the synthesis of peptides containing dehydrovaline and dehydroisoleucine based on copper-mediated enamide formation

  • Franziska Gille and
  • Andreas Kirschning

Beilstein J. Org. Chem. 2016, 12, 564–570, doi:10.3762/bjoc.12.55

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Published 22 Mar 2016
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