Literature DB >> 19473018

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

Juana Du1, Tehshik P Yoon.   

Abstract

Efficient [2+2] heterodimerizations of dissimilar acyclic enones can be accomplished upon visible light irradiation in the presence of a ruthenium(II) photocatalyst. Similar cycloadditions under standard UV photolysis conditions are inefficient and unselective. Nevertheless, a diverse range of unsymmetrical tri- and tetrasubstituted cyclobutane structures can be produced in good yields and excellent diastereoselectivities using this new method. The reaction is promoted by any visible light source, and efficient, gram-scale cycloadditions can be conducted upon irradiating with ambient sunlight.

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Year:  2009        PMID： 19473018      PMCID： PMC2761970          DOI： 10.1021/ja903732v

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


  7 in total

1.  A diastereoselective metal-catalyzed [2+2] cycloaddition of bis-enomes.

Authors:  T G Baik; A L Luis; L C Wang; M J Krische
Journal:  J Am Chem Soc       Date:  2001-07-11       Impact factor: 15.419

2.  Photochemical reactions as key steps in organic synthesis.

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

3.  Anion radical chain cycloaddition of tethered enones: intramolecular cyclobutanation and Diels-Alder cycloaddition.

Authors:  Yeonsuk Roh; Hye-Young Jang; Vincent Lynch; Nathan L Bauld; Michael J Krische
Journal:  Org Lett       Date:  2002-02-21       Impact factor: 6.005

4.  Anion radical [2 + 2] cycloaddition as a mechanistic probe: stoichiometry- and concentration-dependent partitioning of electron-transfer and alkylation pathways in the reaction of the Gilman reagent Me2CuLi.LiI with bis(enones).

Authors:  Jingkui Yang; David F Cauble; Adam J Berro; Nathan L Bauld; Michael J Krische
Journal:  J Org Chem       Date:  2004-11-12       Impact factor: 4.354

5.  Diastereoselective cycloreductions and cycloadditions catalyzed by Co(dpm)(2)-silane (dpm = 2,2,6,6-tetramethylheptane-3,5-dionate): mechanism and partitioning of hydrometallative versus anion radical pathways.

Authors:  Long-Cheng Wang; Hye-Young Jang; Yeonsuk Roh; Vincent Lynch; Arthur J Schultz; Xiaoping Wang; Michael J Krische
Journal:  J Am Chem Soc       Date:  2002-08-14       Impact factor: 15.419

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.  Chemically induced anion radical cycloadditions: intramolecular cyclobutanation of bis(enones) via homogeneous electron transfer.

Authors:  Jingkui Yang; Greg A N Felton; Nathan L Bauld; Michael J Krische
Journal:  J Am Chem Soc       Date:  2004-02-18       Impact factor: 15.419
  7 in total
  55 in total

1.  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

2.  Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-11-08       Impact factor: 15.419

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

Review 4.  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

5.  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

6.  [2+2] cycloadditions by oxidative visible light photocatalysis.

Authors:  Michael A Ischay; Zhan Lu; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2010-06-30       Impact factor: 15.419

7.  Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica.

Authors:  E Paige Stout; Yong-Gang Wang; Daniel Romo; Tadeusz F Molinski
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

8.  A dual-catalysis approach to enantioselective [2 + 2] photocycloadditions using visible light.

Authors:  Juana Du; Kazimer L Skubi; Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-04-25       Impact factor: 47.728

Review 9.  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

Review 10.  Solar synthesis: prospects in visible light photocatalysis.

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