Literature DB >> 20527886

[2+2] cycloadditions by oxidative visible light photocatalysis.

Michael A Ischay1, Zhan Lu, Tehshik P Yoon.   

Abstract

Photochemical reactions are remarkable for their ability to easily assemble cyclobutanes and other strained ring systems that are difficult to construct using other conventional synthetic methods. We have previously shown that Ru(bpy)(3)(2+) is an efficient photocatalyst that promotes the [2+2] cycloadditions of electron-deficient olefins with visible light. Here, we show that Ru(bpy)(3)(2+) is also an effective photocatalyst for the [2+2] cycloaddition of electron-rich olefins. This transformation is enabled by the versatile photoelectrochemical properties of Ru(bpy)(3)(2+), which enables either one-electron reduction or one-electron oxidation of interesting organic substrates under appropriate conditions.

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Year:  2010        PMID: 20527886      PMCID: PMC2892825          DOI: 10.1021/ja103934y

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


  12 in total

1.  Enantiomerically pure cyclobutane derivatives and their use in organic synthesis.

Authors:  Edward Lee-Ruff; Gabriela Mladenova
Journal:  Chem Rev       Date:  2003-04       Impact factor: 60.622

Review 2.  Photocatalysis for the formation of the C-C bond.

Authors:  Maurizio Fagnoni; Daniele Dondi; Davide Ravelli; Angelo Albini
Journal:  Chem Rev       Date:  2007-05-27       Impact factor: 60.622

3.  Photochemical reactions as key steps in organic synthesis.

Authors:  Norbert Hoffmann
Journal:  Chem Rev       Date:  2008-02-27       Impact factor: 60.622

Review 4.  Bioactive cyclobutane-containing alkaloids.

Authors:  Valery M Dembitsky
Journal:  J Nat Med       Date:  2007-09-05       Impact factor: 2.343

5.  Electron transfer photoredox catalysis: intramolecular radical addition to indoles and pyrroles.

Authors:  Joseph W Tucker; Jagan M R Narayanam; Scott W Krabbe; Corey R J Stephenson
Journal:  Org Lett       Date:  2010-01-15       Impact factor: 6.005

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

Authors:  Michael A Ischay; Mary E Anzovino; Juana Du; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2008-09-04       Impact factor: 15.419

7.  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

8.  Visible-light photoredox catalysis: aza-Henry reactions via C-H functionalization.

Authors:  Allison G Condie; José C González-Gómez; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2010-02-10       Impact factor: 15.419

9.  Enantioselective alpha-trifluoromethylation of aldehydes via photoredox organocatalysis.

Authors:  David A Nagib; Mark E Scott; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2009-08-12       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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  49 in total

1.  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 2.  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

3.  Photoinduced Cleavage of N-N Bonds of Aromatic Hydrazines and Hydrazides by Visible Light.

Authors:  Mingzhao Zhu; Nan Zheng
Journal:  Synthesis (Stuttg)       Date:  2011-06-21       Impact factor: 3.157

4.  Endoperoxide synthesis by photocatalytic aerobic [2 + 2 + 2] cycloadditions.

Authors:  Jonathan D Parrish; Michael A Ischay; Zhan Lu; Song Guo; Noël R Peters; Tehshik P Yoon
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

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

Authors:  Megan A Cismesia; Michael A Ischay; Tehshik P Yoon
Journal:  Synthesis (Stuttg)       Date:  2013-10-01       Impact factor: 3.157

6.  Visible-light photoredox catalysis in flow.

Authors:  Joseph W Tucker; Yuan Zhang; Timothy F Jamison; Corey R J Stephenson
Journal:  Angew Chem Int Ed Engl       Date:  2012-03-16       Impact factor: 15.336

7.  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

8.  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

9.  Syntheses of Sceptrins and Nakamuric Acid and Insights into the Biosyntheses of Pyrrole-Imidazole Dimers.

Authors:  Xiaolei Wang; Yang Gao; Zhiqiang Ma; Rodrigo A Rodriguez; Zhi-Xiang Yu; Chuo Chen
Journal:  Org Chem Front       Date:  2015-08-01       Impact factor: 5.281

10.  Visible light photocatalysis of [2+2] styrene cycloadditions by energy transfer.

Authors:  Zhan Lu; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-10       Impact factor: 15.336

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