Literature DB >> 22422343

A walk around the A3-coupling.

Vsevolod A Peshkov1, Olga P Pereshivko, Erik V Van der Eycken.   

Abstract

In recent years, the transition-metal catalyzed three-component coupling of an aldehyde, an alkyne and an amine, commonly called A(3)-coupling, has been established as a convenient and general approach towards propargylamines. Furthermore, the A(3)-coupling has found a broad application as a key step in the construction of various nitrogen-containing heterocycles, biologically active compounds and natural products. Several interesting modifications of the A(3)-coupling as well as different tandem reactions involving A(3)-coupling have been developed. This tutorial review aims to highlight the current achievements in the field of A(3)-couplings and related transformations.

Entities:  

Year:  2012        PMID: 22422343     DOI: 10.1039/c2cs15356d

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  36 in total

1.  Triazole-gold (TAAu) catalyzed three-component coupling (A3 reaction) towards the synthesis of 2, 4-disubstituted quinoline derivatives.

Authors:  Fusong Zhang; Qi Lai; Xiaodong Shi; Zhiguang Song
Journal:  Chin Chem Lett       Date:  2018-05-24       Impact factor: 6.779

2.  The Redox-A3 Reaction.

Authors:  Daniel Seidel
Journal:  Org Chem Front       Date:  2014-06-01       Impact factor: 5.281

Review 3.  On-resin multicomponent protocols for biopolymer assembly and derivatization.

Authors:  Daniel G Rivera; Manuel G Ricardo; Aldrin V Vasco; Ludger A Wessjohann; Erik V Van der Eycken
Journal:  Nat Protoc       Date:  2021-01-20       Impact factor: 13.491

Review 4.  Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors:  Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2013-01-10       Impact factor: 60.622

5.  Chemoselective amination of propargylic C(sp³)-H bonds by cobalt(II)-based metalloradical catalysis.

Authors:  Hongjian Lu; Chaoqun Li; Huiling Jiang; Christopher L Lizardi; X Peter Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-19       Impact factor: 15.336

6.  Catalytic Enantioselective Cyclopropylalkynylation of Aldimines Generated In Situ from α-Amido Sulfones.

Authors:  Alicia Monleón; Gonzalo Blay; José R Pedro
Journal:  Molecules       Date:  2022-06-11       Impact factor: 4.927

7.  Redox-neutral copper(II) carboxylate catalyzed α-alkynylation of amines.

Authors:  Deepankar Das; Aaron X Sun; Daniel Seidel
Journal:  Angew Chem Int Ed Engl       Date:  2013-02-25       Impact factor: 15.336

8.  Convergent Synthesis of α-Branched Amines by Transition-Metal-Catalyzed C-H Bond Additions to Imines.

Authors:  Joshua R Hummel; Jonathan A Ellman
Journal:  Isr J Chem       Date:  2017-06-29       Impact factor: 3.333

9.  Tandem aldehyde-alkyne-amine coupling/cycloisomerization: A new synthesis of coumarins.

Authors:  Maddi Sridhar Reddy; Nuligonda Thirupathi; Madala Haribabu
Journal:  Beilstein J Org Chem       Date:  2013-01-28       Impact factor: 2.883

10.  A(3)-Coupling catalyzed by robust Au nanoparticles covalently bonded to HS-functionalized cellulose nanocrystalline films.

Authors:  Jian-Lin Huang; Derek G Gray; Chao-Jun Li
Journal:  Beilstein J Org Chem       Date:  2013-07-10       Impact factor: 2.883

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