Literature DB >> 25155300

Photocatalytic synthesis of dihydrobenzofurans by oxidative [3+2] cycloaddition of phenols.

Travis R Blum1, Ye Zhu, Sarah A Nordeen, Tehshik P Yoon.   

Abstract

We report a protocol for oxidative [3+2] cycloadditions of phenols and alkenes applicable to the modular synthesis of a large family of dihydrobenzofuran natural products. Visible-light-activated transition metal photocatalysis enables the use of ammonium persulfate as an easily handled, benign terminal oxidant. The broad range of organic substrates that are readily oxidized by photoredox catalysis suggests that this strategy may be applicable to a variety of useful oxidative transformations.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cycloaddition; heterocycles; phenols; photocatalysis; photooxidation

Mesh:

Substances:

Year:  2014        PMID: 25155300      PMCID: PMC4220618          DOI: 10.1002/anie.201406393

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  21 in total

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

Authors:  Jagan M R Narayanam; Corey R J Stephenson
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Review 2.  Natural stilbenes: an overview.

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Journal:  Nat Prod Rep       Date:  2009-06-01       Impact factor: 13.423

3.  Visible-light-induced oxidation/[3+2] cycloaddition/oxidative aromatization sequence: a photocatalytic strategy to construct pyrrolo[2,1-a]isoquinolines.

Authors:  You-Quan Zou; Liang-Qiu Lu; Liang Fu; Ning-Jie Chang; Jian Rong; Jia-Rong Chen; Wen-Jing Xiao
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-22       Impact factor: 15.336

4.  COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans.

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Journal:  Bioorg Med Chem Lett       Date:  2009-10-20       Impact factor: 2.823

Review 5.  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

6.  Eosin Y catalyzed visible light oxidative C-C and C-P bond formation.

Authors:  Durga Prasad Hari; Burkhard König
Journal:  Org Lett       Date:  2011-07-11       Impact factor: 6.005

7.  Friedel-Crafts amidoalkylation via thermolysis and oxidative photocatalysis.

Authors:  Chunhui Dai; Francesco Meschini; Jagan M R Narayanam; Corey R J Stephenson
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8.  Scope, limitations and mechanistic aspects of the photo-induced cross-linking of proteins by water-soluble metal complexes.

Authors:  D A Fancy; C Denison; K Kim; Y Xie; T Holdeman; F Amini; T Kodadek
Journal:  Chem Biol       Date:  2000-09

9.  Three new 7.3',8.5'-connected bicyclo[3.2.1]octanoids and other neolignans from leaves of Nectandra amazonum NEES. (Lauraceae).

Authors:  Ericsson David Coy Barrera; Luis Enrique Cuca Suárez
Journal:  Chem Pharm Bull (Tokyo)       Date:  2009-06       Impact factor: 1.645

10.  Visible-light photoredox catalysis enabled bromination of phenols and alkenes.

Authors:  Yating Zhao; Zhe Li; Chao Yang; Run Lin; Wujiong Xia
Journal:  Beilstein J Org Chem       Date:  2014-03-07       Impact factor: 2.883

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  16 in total

1.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

Review 2.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

3.  Catalytic Oxidative Coupling of Phenols and Related Compounds.

Authors:  Jingze Wu; Marisa C Kozlowski
Journal:  ACS Catal       Date:  2022-05-18       Impact factor: 13.700

4.  Photocatalytic Oxidative Dearomatization of Orcinaldehyde Derivatives.

Authors:  Summer A Baker Dockrey; Alison R H Narayan
Journal:  Org Lett       Date:  2020-04-15       Impact factor: 6.005

5.  Advances in Photocatalysis: A Microreview of Visible Light Mediated Ruthenium and Iridium Catalyzed Organic Transformations.

Authors:  Jon I Day; Kip Teegardin; Jimmie Weaver; John Chan
Journal:  Org Process Res Dev       Date:  2016-06-28       Impact factor: 3.317

6.  Oxidative Photocatalytic Homo- and Cross-Coupling of Phenols: Nonenzymatic, Catalytic Method for Coupling Tyrosine.

Authors:  Kyle A Niederer; Philip H Gilmartin; Marisa C Kozlowski
Journal:  ACS Catal       Date:  2020-11-25       Impact factor: 13.084

Review 7.  Oxidase reactions in photoredox catalysis.

Authors:  Nicholas L Reed; Tehshik P Yoon
Journal:  Chem Soc Rev       Date:  2021-01-25       Impact factor: 54.564

8.  Arylsulfonylacetamides as bifunctional reagents for alkene aminoarylation.

Authors:  Timothy M Monos; Rory C McAtee; Corey R J Stephenson
Journal:  Science       Date:  2018-09-28       Impact factor: 63.714

9.  Catalytic asymmetric total syntheses of myrtucommuacetalone, myrtucommuacetalone B, and callistrilones A, C, D and E.

Authors:  Min-Jing Cheng; Jia-Qing Cao; Xin-Yi Yang; Li-Ping Zhong; Li-Jun Hu; Xi Lu; Bao-Long Hou; Ya-Jian Hu; Ying Wang; Xue-Fu You; Lei Wang; Wen-Cai Ye; Chuang-Chuang Li
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

10.  Direct α-heteroarylation of amides (α to nitrogen) and ethers through a benzaldehyde-mediated photoredox reaction.

Authors:  Yongqiang Zhang; Kevin B Teuscher; Haitao Ji
Journal:  Chem Sci       Date:  2015-12-07       Impact factor: 9.825

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