Literature DB >> 24985967

[2+2] cycloaddition of 1,3-dienes by visible light photocatalysis.

Anna E Hurtley1, Zhan Lu, Tehshik P Yoon.   

Abstract

[2+2] photocycloadditions of 1,3-dienes represent a powerful yet synthetically underutilized class of reactions. We report that visible light absorbing transition metal complexes enable the [2+2] cycloaddition of a diverse range of 1,3-dienes. The ability to use long-wavelength visible light is attractive because these reaction conditions tolerate the presence of sensitive functional groups that might be readily decomposed by the high-energy UVC radiation required for direct photoexcitation of 1,3-dienes. The resulting vinylcyclobutane products are poised for a variety of further diversification reactions, and this method is consequently expected to be powerfully enabling in the synthesis of complex organic targets.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cycloadditions; energy transfer; photochemistry; small ring systems; total synthesis

Mesh:

Year:  2014        PMID: 24985967      PMCID: PMC4134740          DOI: 10.1002/anie.201405359

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


  21 in total

1.  Photochemical reactions as key steps in organic synthesis.

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

Review 2.  Bioactive cyclobutane-containing alkaloids.

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

Review 3.  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

4.  Radical cation Diels-Alder cycloadditions by visible light photocatalysis.

Authors:  Shishi Lin; Michael A Ischay; Charles G Fry; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2011-11-11       Impact factor: 15.419

5.  Visible Light Photocatalysis of Radical Anion Hetero-Diels-Alder Cycloadditions.

Authors:  Anna E Hurtley; Megan A Cismesia; Michael A Ischay; Tehshik P Yoon
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

6.  Cyclobutanes in catalysis.

Authors:  Tobias Seiser; Tanguy Saget; Duc N Tran; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-26       Impact factor: 15.336

7.  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

8.  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

9.  Crossed Intermolecular [2+2] Cycloaddition of Styrenes by Visible Light Photocatalysis.

Authors:  Michael A Ischay; Michael S Ament; Tehshik P Yoon
Journal:  Chem Sci       Date:  2012-06-25       Impact factor: 9.825

10.  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

View more
  20 in total

1.  Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Authors:  Mikayo Hayashi; Lauren E Brown; John A Porco
Journal:  European J Org Chem       Date:  2016-10

2.  Enantioselective Excited-State Photoreactions Controlled by a Chiral Hydrogen-Bonding Iridium Sensitizer.

Authors:  Kazimer L Skubi; Jesse B Kidd; Hoimin Jung; Ilia A Guzei; Mu-Hyun Baik; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2017-11-16       Impact factor: 15.419

3.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

4.  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

5.  Spin-Selective Generation of Triplet Nitrenes: Olefin Aziridination through Visible-Light Photosensitization of Azidoformates.

Authors:  Spencer O Scholz; Elliot P Farney; Sangyun Kim; Desiree M Bates; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-06       Impact factor: 15.336

6.  Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters.

Authors:  Spencer O Scholz; Jesse B Kidd; Luca Capaldo; Niecia E Flikweert; Rowan M Littlefield; Tehshik P Yoon
Journal:  Org Lett       Date:  2021-04-12       Impact factor: 6.005

Review 7.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

8.  Cobalt-Catalyzed [2π + 2π] Cycloadditions of Alkenes: Scope, Mechanism, and Elucidation of Electronic Structure of Catalytic Intermediates.

Authors:  Valerie A Schmidt; Jordan M Hoyt; Grant W Margulieux; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2015-06-12       Impact factor: 15.419

9.  Chemo- and Stereoselective Intermolecular [2+2] Photocycloaddition of Conjugated Dienes using Colloidal Nanocrystal Photocatalysts.

Authors:  Yishu Jiang; Muwen Yang; Yue Wu; Rafael López-Arteaga; Cameron R Rogers; Emily A Weiss
Journal:  Chem Catal       Date:  2021-03-02

10.  Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F.

Authors:  S L Drew; A L Lawrence; M S Sherburn
Journal:  Chem Sci       Date:  2015-05-07       Impact factor: 9.825

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.