Literature DB >> 24154547

Impact of copper-catalyzed cross-coupling reactions in natural product synthesis: the emergence of new retrosynthetic paradigms.

Gwilherm Evano1, Cédric Theunissen, Alexandre Pradal.   

Abstract

Copper-catalyzed Ullmann-Goldberg-type cross-coupling reactions have undergone nothing short of a renaissance over the last decade and an impressive number of procedures are now available for the formation of C-N, C-O and C-S bonds with remarkable efficiencies and surgical precision. These reactions have been recently integrated into natural product synthesis, which clearly resulted in the emergence of new retrosynthetic paradigms and bond disconnections. The impact of copper-catalyzed cross-coupling reactions in natural product synthesis will be overviewed in this article with an emphasis on the evolution of strategies due to copper catalysis, mostly by comparison with alternative tactics and their relative efficiencies.

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Year:  2013        PMID: 24154547     DOI: 10.1039/c3np70071b

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  11 in total

1.  Deconvoluting the Innocent vs. Non-innocent Behavior of N,N-diethylphenylazothioformamide Ligands with Copper Sources.

Authors:  Nicolas A Johnson; Samuel R Wolfe; Humayun Kabir; Gabriel A Andrade; Glenn P A Yap; Zachariah M Heiden; James G Moberly; Mark F Roll; Kristopher V Waynant
Journal:  Eur J Inorg Chem       Date:  2017-11-26       Impact factor: 2.524

2.  Synthesis, characterisation and reactivity of copper(I) amide complexes and studies on their role in the modified Ullmann amination reaction.

Authors:  Simon Sung; D Christopher Braddock; Alan Armstrong; Colin Brennan; David Sale; Andrew J P White; Robert P Davies
Journal:  Chemistry       Date:  2015-03-18       Impact factor: 5.236

3.  Synthesis of (diarylmethyl)amines using Ni-catalyzed arylation of C(sp3)-H bonds.

Authors:  José A Fernández-Salas; Enrico Marelli; Steven P Nolan
Journal:  Chem Sci       Date:  2015-06-22       Impact factor: 9.825

4.  A Synthesis of Substituted α-Allenols via Iron-Catalyzed Cross-Coupling of Propargyl Carboxylates with Grignard Reagents.

Authors:  Simon N Kessler; Fabian Hundemer; Jan-E Bäckvall
Journal:  ACS Catal       Date:  2016-09-28       Impact factor: 13.084

5.  Total synthesis of the reported structure of ceanothine D via a novel macrocyclization strategy.

Authors:  Jisun Lee; Madeleine M Joullié
Journal:  Chem Sci       Date:  2018-01-31       Impact factor: 9.825

6.  Cross dehydrogenative C-O coupling catalysed by a catenane-coordinated copper(i).

Authors:  Lihui Zhu; Jiasheng Li; Jun Yang; Ho Yu Au-Yeung
Journal:  Chem Sci       Date:  2020-11-01       Impact factor: 9.825

7.  Nickel-Catalyzed Arylation of Heteroaryl-containing Diarylmethanes: Exceptional Reactivity of the Ni(NIXANTPHOS)-based Catalyst.

Authors:  Xinyu Cao; Sheng-Chun Sha; Minyan Li; Byeong-Seon Kim; Catherine Morgan; Rudan Huang; Xiaodong Yang; Patrick J Walsh
Journal:  Chem Sci       Date:  2015-10-26       Impact factor: 9.825

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

Authors:  Franziska Gille; Andreas Kirschning
Journal:  Beilstein J Org Chem       Date:  2016-03-22       Impact factor: 2.883

9.  Synthesis of Azacarbolines via PhIO2-Promoted Intramolecular Oxidative Cyclization of α-Indolylhydrazones.

Authors:  Matteo Corrieri; Lucia De Crescentini; Fabio Mantellini; Giacomo Mari; Stefania Santeusanio; Gianfranco Favi
Journal:  J Org Chem       Date:  2021-12-06       Impact factor: 4.354

10.  Synthesis of MAPA Reagents and 2-Alkyl(aryl)aminopyridines from 2-Bromopyridine Using the Goldberg Reaction.

Authors:  Daniel L Comins
Journal:  Molecules       Date:  2022-03-11       Impact factor: 4.411

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