Literature DB >> 25143660

Reductive Cyclizations of Nitroarenes to Hydroxamic Acids by Visible Light Photoredox Catalysis.

Megan A Cismesia1, Michael A Ischay1, Tehshik P Yoon1.   

Abstract

We have developed a photocatalytic reduction of nitroarenes as an efficient, chemoselective route to biologically important N-phenyl hydroxamic acid scaffolds. Optimal conditions call for 2.5 mol% of a ruthenium photocatalyst, visible light irradiation, and a dihydropyridine terminal reductant. Because of the mild nature of the visible light activation, functional groups that might be sensitive to other non-photochemical reduction methods are easily tolerated.

Entities:  

Keywords:  electron transfer; heterocycles; hydroxamic acids; photochemistry; reduction

Year:  2013        PMID： 25143660      PMCID： PMC4134921          DOI： 10.1055/s-0033-1338419

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN： 0039-7881            Impact factor:   3.157


  27 in total

1.  SYNTHESIS AND MICROBIOLOGICAL PROPERTIES OF 3-AMINO-3,4-DIHYDRO-1-HYDROXYCARBOSTYRIL.

Authors:  A L DAVIS; O H CHOUN; D E COOK; T J MCCORD
Journal:  J Med Chem       Date:  1964-09       Impact factor: 7.446

2.  Visible light photoredox catalysis: applications in organic synthesis.

Authors:  Jagan M R Narayanam; Corey R J Stephenson
Journal:  Chem Soc Rev       Date:  2010-06-08       Impact factor: 54.564

3.  Photoredox catalysis with visible light.

Authors:  Kirsten Zeitler
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Synthesis and antibacterial activities of some chloro analogs of 3 amino-3,4-dihydro-1-hydroxycarbostyril.

Authors:  A L Davis; W H Chambers; D H Kelley; D A Fell; J R Haynes; K L Hulme; L D Gage; T J McCord
Journal:  J Med Chem       Date:  1975-07       Impact factor: 7.446

5.  A general strategy for the synthesis of cyclic N-aryl hydroxamic acids via partial nitro group reduction.

Authors:  Laura A McAllister; Bruce M Bechle; Amy B Dounay; Edelweiss Evrard; Xinmin Gan; Somraj Ghosh; Ji-Young Kim; Vinod D Parikh; Jamison B Tuttle; Patrick R Verhoest
Journal:  J Org Chem       Date:  2011-04-11       Impact factor: 4.354

6.  Synthesis of novel KDR kinase inhibitors through catalytic reductive cyclization of o-nitrobenzylcarbonyl compounds.

Authors:  Audrey Wong; Jeffrey T Kuethe; Ian W Davies; David L Hughes
Journal:  J Org Chem       Date:  2004-10-29       Impact factor: 4.354

7.  A general synthesis of N-hydroxyindoles.

Authors:  Audrey Wong; Jeffrey T Kuethe; Ian W Davies
Journal:  J Org Chem       Date:  2003-12-12       Impact factor: 4.354

8.  Crossed Intermolecular [2+2] Cycloaddition of Styrenes by Visible Light Photocatalysis.

Authors:  Michael A Ischay; Michael S Ament; Tehshik P Yoon
Journal:  Chem Sci       Date:  2012-06-25       Impact factor: 9.825

9.  Crossed intermolecular [2+2] cycloadditions of acyclic enones via visible light photocatalysis.

Authors:  Juana Du; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2009-10-21       Impact factor: 15.419

10.  Electron-transfer photoredox catalysis: development of a tin-free reductive dehalogenation reaction.

Authors:  Jagan M R Narayanam; Joseph W Tucker; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2009-07-01       Impact factor: 15.419
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  1 in total

Review 1.  Dual Catalysis Strategies in Photochemical Synthesis.

Authors:  Kazimer L Skubi; Travis R Blum; Tehshik P Yoon
Journal:  Chem Rev       Date:  2016-04-25       Impact factor: 60.622
  1 in total

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