Literature DB >> 35431717

Combined Photoredox and Carbene Catalysis for the Synthesis of γ-Aryloxy Ketones.

Pengzhi Wang1, Keegan P Fitzpatrick1, Karl A Scheidt1.   

Abstract

N-heterocyclic carbenes (NHCs) have emerged as catalysts for the construction of C-C bonds in the synthesis of substituted ketones under single-electron processes. Despite these recent reports, there still remains a need to increase the utility and practicality of these reactions by exploring new radical coupling partners. Herein, we report the synthesis of γ-aryloxyketones via combined NHC/photoredox catalysis. In this reaction, an α-aryloxymethyl radical is generated via oxidation of an aryloxymethyl potassium trifluoroborate salt, which is then added into styrene derivatives to provide a stabilized benzylic radical. Subsequent radical-radical coupling reaction with an azolium radical affords the γ-aryloxy ketone products.

Entities:  

Keywords:  N-heterocyclic carbene; acyl azolium; photochemistry; potassium trifluoroborate; radical relay

Year:  2021        PMID: 35431717      PMCID: PMC9012476          DOI: 10.1002/adsc.202101354

Source DB:  PubMed          Journal:  Adv Synth Catal        ISSN: 1615-4150            Impact factor:   5.981


  41 in total

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4.  An overview of N-heterocyclic carbenes.

Authors:  Matthew N Hopkinson; Christian Richter; Michael Schedler; Frank Glorius
Journal:  Nature       Date:  2014-06-26       Impact factor: 49.962

5.  Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds.

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6.  Photoredox Cross-Coupling: Ir/Ni Dual Catalysis for the Synthesis of Benzylic Ethers.

Authors:  Idris Karakaya; David N Primer; Gary A Molander
Journal:  Org Lett       Date:  2015-06-16       Impact factor: 6.005

7.  Aryl radical-mediated N-heterocyclic carbene catalysis.

Authors:  Yuki Matsuki; Nagisa Ohnishi; Yuki Kakeno; Shunsuke Takemoto; Takuya Ishii; Kazunori Nagao; Hirohisa Ohmiya
Journal:  Nat Commun       Date:  2021-06-22       Impact factor: 14.919

8.  Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates.

Authors:  Joshua L Zhu; Karl A Scheidt
Journal:  Tetrahedron       Date:  2021-06-16       Impact factor: 2.388

9.  Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates.

Authors:  Matthieu Jouffroy; David N Primer; Gary A Molander
Journal:  J Am Chem Soc       Date:  2015-12-24       Impact factor: 15.419

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  3 in total

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2.  Carbene and photocatalyst-catalyzed decarboxylative radical coupling of carboxylic acids and acyl imidazoles to form ketones.

Authors:  Shi-Chao Ren; Xing Yang; Bivas Mondal; Chengli Mou; Weiyi Tian; Zhichao Jin; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2022-05-23       Impact factor: 17.694

3.  Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans.

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  3 in total

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