Literature DB >> 21192632

Visible-light photoredox catalysis: dehalogenation of vicinal dibromo-, α-halo-, and α,α-dibromocarbonyl compounds.

Tapan Maji1, Ananta Karmakar, Oliver Reiser.   

Abstract

vic-Dibromo-, α-halo-, or α,α-dibromocarbonyl compounds can be efficiently dehalogenated using catalytic tris(2,2'-bipyridyl)ruthenium dichloride (Ru(bpy)(3)Cl(2)) in combination with 1,5-dimethoxynaphthalene (DMN) and ascorbate as sacrificial electron donor. For this process, a visible light promoted photocatalytic cycle is proposed that involves the reduction of carbon halogen bonds via free radical intermediates.

Entities:  

Year:  2010        PMID: 21192632     DOI: 10.1021/jo102239x

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  12 in total

1.  Functionally diverse nucleophilic trapping of iminium intermediates generated utilizing visible light.

Authors:  David B Freeman; Laura Furst; Allison G Condie; Corey R J Stephenson
Journal:  Org Lett       Date:  2011-12-08       Impact factor: 6.005

2.  Total synthesis of (+)-gliocladin C enabled by visible-light photoredox catalysis.

Authors:  Laura Furst; Jagan M R Narayanam; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-12       Impact factor: 15.336

Review 3.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

4.  Visible Light Photocatalysis of Radical Anion Hetero-Diels-Alder Cycloadditions.

Authors:  Anna E Hurtley; Megan A Cismesia; Michael A Ischay; Tehshik P Yoon
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

5.  Intermolecular [3+2] cycloaddition of cyclopropylamines with olefins by visible-light photocatalysis.

Authors:  Soumitra Maity; Mingzhao Zhu; Ryan Spencer Shinabery; Nan Zheng
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-23       Impact factor: 15.336

6.  A Photo Touch on Amines: New Synthetic Adventures of Nitrogen Radical Cations.

Authors:  Soumitira Maity; Nan Zheng
Journal:  Synlett       Date:  2012-07-23       Impact factor: 2.454

7.  Aryl dechlorination and defluorination with an organic super-photoreductant.

Authors:  Felix Glaser; Christopher B Larsen; Christoph Kerzig; Oliver S Wenger
Journal:  Photochem Photobiol Sci       Date:  2020-06-26       Impact factor: 3.982

8.  A visible-light-mediated oxidative C-N bond formation/aromatization cascade: photocatalytic preparation of N-arylindoles.

Authors:  Soumitra Maity; Nan Zheng
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-22       Impact factor: 15.336

9.  Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions.

Authors:  Haigen Fu; Heather Lam; Megan A Emmanuel; Ji Hye Kim; Braddock A Sandoval; Todd K Hyster
Journal:  J Am Chem Soc       Date:  2021-06-11       Impact factor: 16.383

10.  Diastereoselective Additions of Allylmagnesium Reagents to α-Substituted Ketones When Stereochemical Models Cannot Be Used.

Authors:  Nicole D Bartolo; Krystyna M Demkiw; Elizabeth M Valentín; Chunhua T Hu; Alya A Arabi; K A Woerpel
Journal:  J Org Chem       Date:  2021-05-12       Impact factor: 4.198

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