Literature DB >> 24678625

Facile synthesis of Z-alkenes via uphill catalysis.

Kamaljeet Singh1, Shannon J Staig, Jimmie D Weaver.   

Abstract

Catalytic access to thermodynamically less stable Z-alkenes has recently received considerable attention. These approaches have relied upon kinetic control of the reaction to arrive at the thermodynamically less stable geometrical isomer. Herein, we present an orthogonal approach which proceeds via photochemically catalyzed isomerization of the thermodynamic E-alkene to the less stable Z-isomer which occurs via a photochemical pumping mechanism. We consider two potential mechanisms. Importantly, the reaction conditions are mild, tolerant, and operationally simple and will be easily implemented.

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Year:  2014        PMID: 24678625     DOI: 10.1021/ja5019749

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


  46 in total

1.  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

2.  A Redox Strategy for Light-Driven, Out-of-Equilibrium Isomerizations and Application to Catalytic C-C Bond Cleavage Reactions.

Authors:  Eisuke Ota; Huaiju Wang; Nils Lennart Frye; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2019-01-15       Impact factor: 15.419

3.  Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control.

Authors:  Mohammad B Khaled; Roukaya K El Mokadem; Jimmie D Weaver
Journal:  J Am Chem Soc       Date:  2017-09-08       Impact factor: 15.419

4.  Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3 )-H Sites of Alcohols.

Authors:  Padon Chuentragool; Dongari Yadagiri; Taiki Morita; Sumon Sarkar; Marvin Parasram; Yang Wang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-17       Impact factor: 15.336

5.  Z-isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis.

Authors:  Shirin Kahremany; Christopher Lane Sander; Gregory P Tochtrop; Adam Kubas; Krzysztof Palczewski
Journal:  Org Biomol Chem       Date:  2019-08-28       Impact factor: 3.876

6.  Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes.

Authors:  Bin Xu; Ludovic Troian-Gautier; Ryan Dykstra; Robert T Martin; Osvaldo Gutierrez; Uttam K Tambar
Journal:  J Am Chem Soc       Date:  2020-03-19       Impact factor: 15.419

7.  Photocatalytic C-F Reduction and Functionalization.

Authors:  Sameera Senaweera; Jimmie D Weaver
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

8.  Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α-Amino C-H Arylation and Epimerization.

Authors:  Morgan M Walker; Brian Koronkiewicz; Shuming Chen; K N Houk; James M Mayer; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2020-04-24       Impact factor: 15.419

9.  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

10.  Bromine Radical Catalysis by Energy Transfer Photosensitization.

Authors:  Dian-Feng Chen; Cameron H Chrisman; Garret M Miyake
Journal:  ACS Catal       Date:  2020-01-30       Impact factor: 13.084

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