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Literature DB >> 24955245

The Redox-A³ Reaction.

Abstract

This Highlight details the recent emergence of a new type of A3 reaction (three-component condensation of an amine, an aldehyde and an alkyne). In contrast to the classic A3 coupling process, the redox-A3 reaction incorporates an iminium isomerization step and leads to amine α-alkynylation. The overall transformation is redox-neutral by virtue of a combined reductive N-alkylation/oxidative C-H bond functionalization.

Entities: Chemical Disease Gene

Year: 2014 PMID： 24955245 PMCID： PMC4061755 DOI： 10.1039/C4QO00022F

Source DB: PubMed Journal: Org Chem Front ISSN： 2052-4110 Impact factor: 5.281

30 in total

1. Intramolecular dipolar cycloaddition reactions of azomethine ylides.

Authors: Iain Coldham; Richard Hufton
Journal: Chem Rev Date: 2005-07 Impact factor: 60.622

2. Construction of enantiopure pyrrolidine ring system via asymmetric [3+2]-cycloaddition of azomethine ylides.

Authors: Ganesh Pandey; Prabal Banerjee; Smita R Gadre
Journal: Chem Rev Date: 2006-11 Impact factor: 60.622

3. The copper-catalyzed decarboxylative coupling of the sp3-hybridized carbon atoms of alpha-amino acids.

Authors: Hai-Peng Bi; Liang Zhao; Yong-Min Liang; Chao-Jun Li
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

4. Synthesis of symmetric 1,4-diamino-2-butynes via a Cu(I)-catalyzed one-pot A3-coupling/decarboxylative coupling of a propiolic acid, an aldehyde, and an amine.

Authors: Huangdi Feng; Denis S Ermolat'ev; Gonghua Song; Erik V Van der Eycken
Journal: J Org Chem Date: 2012-05-11 Impact factor: 4.354

5. The redox-neutral approach to C-H functionalization.

Authors: Bo Peng; Nuno Maulide
Journal: Chemistry Date: 2013-09-11 Impact factor: 5.236

6. Direct α-functionalization of saturated cyclic amines.

Authors: Emily A Mitchell; Aldo Peschiulli; Nicolas Lefevre; Lieven Meerpoel; Bert U W Maes
Journal: Chemistry Date: 2012-07-24 Impact factor: 5.236

7. Microwave-assisted decarboxylative three-component coupling of a 2-oxoacetic acid, an amine, and an alkyne.

Authors: Huangdi Feng; Denis S Ermolat'ev; Gonghua Song; Erik V Van der Eycken
Journal: J Org Chem Date: 2011-08-23 Impact factor: 4.354

8. Regioselective Cu(I)-catalyzed tandem A3-coupling/decarboxylative coupling to 3-amino-1,4-enynes.

Authors: Huangdi Feng; Denis S Ermolat'ev; Gonghua Song; Erik V Van der Eycken
Journal: Org Lett Date: 2012-03-28 Impact factor: 6.005

9. Organocatalytic asymmetric biomimetic transamination: from α-keto esters to optically active α-amino acid derivatives.

Authors: Xiao Xiao; Ying Xie; Cunxiang Su; Mao Liu; Yian Shi
Journal: J Am Chem Soc Date: 2011-08-03 Impact factor: 15.419

10. Nontraditional reactions of azomethine ylides: decarboxylative three-component couplings of alpha-amino acids.

Authors: Chen Zhang; Daniel Seidel
Journal: J Am Chem Soc Date: 2010-02-17 Impact factor: 15.419

20 in total

1. Redox-Annulations of Cyclic Amines with ortho-Cyanomethylbenzaldehydes.

Authors: Anirudra Paul; Hemant S Chandak; Longle Ma; Daniel Seidel
Journal: Org Lett Date: 2020-01-27 Impact factor: 6.005

2. α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines.

Authors: Anirudra Paul; Daniel Seidel
Journal: J Am Chem Soc Date: 2019-05-24 Impact factor: 15.419

3. Redox-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.

Authors: Anirudra Paul; Alafate Adili; Daniel Seidel
Journal: Org Lett Date: 2019-03-06 Impact factor: 6.005

4. An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step.

Authors: Zhengbo Zhu; Daniel Seidel
Journal: Org Lett Date: 2016-01-19 Impact factor: 6.005

5. C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds.

Authors: YoungKu Kang; Matthew T Richers; Conrad H Sawicki; Daniel Seidel
Journal: Chem Commun (Camb) Date: 2015-07-07 Impact factor: 6.222

6. The Rügheimer-Burrows reaction revisited: Facile preparation of 4-alkylisoquinolines and 3,5-dialkylpyridines from (partially) saturated amines.

Authors: Alena Yu Platonova; Daniel Seidel
Journal: Tetrahedron Lett Date: 2015-06 Impact factor: 2.415

7. Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.

Authors: Longle Ma; Anirudra Paul; Martin Breugst; Daniel Seidel
Journal: Chemistry Date: 2016-11-09 Impact factor: 5.236

8. Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.

Authors: Zhengbo Zhu; Hemant S Chandak; Daniel Seidel
Journal: Org Lett Date: 2018-06-25 Impact factor: 6.005

9. α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines.

Authors: Jae Hyun Kim; Anirudra Paul; Ion Ghiviriga; Daniel Seidel
Journal: Org Lett Date: 2021-01-19 Impact factor: 6.005

10. Diversification of Unprotected Alicyclic Amines by C-H Bond Functionalization: Decarboxylative Alkylation of Transient Imines.

Authors: Anirudra Paul; Jae Hyun Kim; Scott D Daniel; Daniel Seidel
Journal: Angew Chem Int Ed Engl Date: 2020-11-17 Impact factor: 15.336