Literature DB >> 18767798

Efficient visible light photocatalysis of [2+2] enone cycloadditions.

Michael A Ischay1, Mary E Anzovino, Juana Du, Tehshik P Yoon.   

Abstract

We report that Ru(bipy)3Cl2 can serve as a visible light photocatalyst for [2+2] enone cycloadditions. A variety of aryl enones participate readily in the reaction, and the diastereoselectivity in the formation of the cyclobutane products is excellent. We propose a mechanism in which a photogenerated Ru(bipy)3+ complex promotes one-electron reduction of the enone substrate, which undergoes subsequent radical anion cycloaddition. The efficiency of this process is extremely high, which allows rapid, high-yielding [2+2] cyclizations to be conducted using incident sunlight as the only source of irradiation.

Entities:  

Year:  2008        PMID: 18767798     DOI: 10.1021/ja805387f

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  104 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.  Visible light photocatalysis as a greener approach to photochemical synthesis.

Authors:  Tehshik P Yoon; Michael A Ischay; Juana Du
Journal:  Nat Chem       Date:  2010-06-23       Impact factor: 24.427

3.  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

4.  Catalytic Radical Domino Reactions in Organic Synthesis.

Authors:  Leanne J Sebren; James J Devery; Corey R J Stephenson
Journal:  ACS Catal       Date:  2014-02-07       Impact factor: 13.084

5.  Transition metal photoredox catalysis of radical thiol-ene reactions.

Authors:  Elizabeth L Tyson; Michael S Ament; Tehshik P Yoon
Journal:  J Org Chem       Date:  2012-11-12       Impact factor: 4.354

Review 6.  Proton-Coupled Electron Transfer in Organic Synthesis: Fundamentals, Applications, and Opportunities.

Authors:  David C Miller; Kyle T Tarantino; Robert R Knowles
Journal:  Top Curr Chem (Cham)       Date:  2016-05-09

7.  Photoredox activation for the direct β-arylation of ketones and aldehydes.

Authors:  Michael T Pirnot; Danica A Rankic; David B C Martin; David W C MacMillan
Journal:  Science       Date:  2013-03-29       Impact factor: 47.728

8.  Brønsted acid cocatalysts in photocatalytic radical addition of α-amino C-H bonds across Michael acceptors.

Authors:  Laura Ruiz Espelt; Eric M Wiensch; Tehshik P Yoon
Journal:  J Org Chem       Date:  2013-04-10       Impact factor: 4.354

Review 9.  Solar synthesis: prospects in visible light photocatalysis.

Authors:  Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-02-28       Impact factor: 47.728

10.  Photoredox Activation and Anion Binding Catalysis in the Dual Catalytic Enantioselective Synthesis of β-Amino Esters.

Authors:  Giulia Bergonzini; Corinna S Schindler; Carl-Johan Wallentin; Eric N Jacobsen; Corey R J Stephenson
Journal:  Chem Sci       Date:  2014-01       Impact factor: 9.825

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