Literature DB >> 29652160

Photoredox-catalyzed Direct Reductive Amination of Aldehydes without an External Hydrogen/Hydride Source.

Rauful Alam1, Gary A Molander1.   

Abstract

The direct reductive amination of aromatic aldehydes has been realized using a photocatalyst under visible light irradiation. The single electron oxidation of an in situ formed aminal species generates the putative α-amino radical that eventually delivers the reductive amination product. This method is operationally simple, highly selective, and functional group tolerant, which allows the direct synthesis of benzylic amines by a unique mechanistic pathway.

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Year:  2018        PMID: 29652160      PMCID: PMC5935552          DOI: 10.1021/acs.orglett.8b00895

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  39 in total

1.  Hydrogen-free reductive amination using iron pentacarbonyl as a reducing agent.

Authors:  Oleg I Afanasyev; Dmitry L Usanov; Denis Chusov
Journal:  Org Biomol Chem       Date:  2017-12-13       Impact factor: 3.876

2.  Visible light photoredox catalysis: generation and addition of N-aryltetrahydroisoquinoline-derived α-amino radicals to Michael acceptors.

Authors:  Paul Kohls; Deepak Jadhav; Ganesh Pandey; Oliver Reiser
Journal:  Org Lett       Date:  2012-01-19       Impact factor: 6.005

3.  Chemo- and Regioselective Organo-Photoredox Catalyzed Hydroformylation of Styrenes via a Radical Pathway.

Authors:  He Huang; Chenguang Yu; Yueteng Zhang; Yongqiang Zhang; Patrick S Mariano; Wei Wang
Journal:  J Am Chem Soc       Date:  2017-07-13       Impact factor: 15.419

4.  Protecting group-free, selective cross-coupling of alkyltrifluoroborates with borylated aryl bromides via photoredox/nickel dual catalysis.

Authors:  Yohei Yamashita; John C Tellis; Gary A Molander
Journal:  Proc Natl Acad Sci U S A       Date:  2015-09-14       Impact factor: 11.205

5.  Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

Authors:  Camille Remeur; Christopher B Kelly; Niki R Patel; Gary A Molander
Journal:  ACS Catal       Date:  2017-08-16       Impact factor: 13.084

6.  Ruthenium-catalyzed reductive amination without an external hydrogen source.

Authors:  Pavel N Kolesnikov; Niyaz Z Yagafarov; Dmitry L Usanov; Victor I Maleev; Denis Chusov
Journal:  Org Lett       Date:  2014-12-31       Impact factor: 6.005

7.  Mechanistic Perspectives on Organic Photoredox Catalysis for Aromatic Substitutions.

Authors:  Michal Majek; Axel Jacobi von Wangelin
Journal:  Acc Chem Res       Date:  2016-09-26       Impact factor: 22.384

8.  Oxygen switch in visible-light photoredox catalysis: radical additions and cyclizations and unexpected C-C-bond cleavage reactions.

Authors:  Shaoqun Zhu; Arindam Das; Lan Bui; Hanjun Zhou; Dennis P Curran; Magnus Rueping
Journal:  J Am Chem Soc       Date:  2013-01-18       Impact factor: 15.419

9.  Synthesis of tertiary arylamines: Lewis acid-catalyzed direct reductive N-alkylation of secondary amines with ketones through an alternative pathway.

Authors:  Onkar S Nayal; Maheshwar S Thakur; Vinod Bhatt; Manoranjan Kumar; Neeraj Kumar; Bikram Singh; Upendra Sharma
Journal:  Chem Commun (Camb)       Date:  2016-07-01       Impact factor: 6.222

10.  Reductive Amination by Photoredox Catalysis and Polarity-Matched Hydrogen Atom Transfer.

Authors:  Xingwei Guo; Oliver S Wenger
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-18       Impact factor: 15.336

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  2 in total

1.  Mechanochemistry Activated Covalent Conjugation Reactions in Soft Hydrogels Induced by Interfacial Failure.

Authors:  Ashray V Parameswar; Karan V Dikshit; Sanli Movafaghi; Carson J Bruns; Andrew P Goodwin
Journal:  ACS Appl Mater Interfaces       Date:  2020-12-28       Impact factor: 9.229

2.  Enantioselective synthesis of amines by combining photoredox and enzymatic catalysis in a cyclic reaction network.

Authors:  Xingwei Guo; Yasunori Okamoto; Mirjam R Schreier; Thomas R Ward; Oliver S Wenger
Journal:  Chem Sci       Date:  2018-05-17       Impact factor: 9.825

  2 in total

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