Literature DB >> 31010292

Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis.

Cédric Theunissen1, Melissa A Ashley1, Tomislav Rovis1.   

Abstract

Olefin metathesis is now one of the most efficient ways to create new carbon-carbon bonds. While most efforts focused on the development of ever-more efficient catalysts, a particular attention has recently been devoted to developing latent metathesis catalysts, inactive species that need an external stimulus to become active. This furnishes an increased control over the reaction which is crucial for applications in materials science. Here, we report our work on the development of a new system to achieve visible-light-controlled metathesis by merging olefin metathesis and photoredox catalysis. The combination of a ruthenium metathesis catalyst bearing two N-heterocyclic carbenes with an oxidizing pyrylium photocatalyst affords excellent temporal and spatial resolution using only visible light as stimulus. Applications of this system in synthesis, as well as in polymer patterning and photolithography with spatially resolved ring-opening metathesis polymerization, are described.

Entities:  

Year:  2019        PMID: 31010292      PMCID: PMC7097883          DOI: 10.1021/jacs.8b13663

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


  37 in total

1.  The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.

Authors:  T M Trnka; R H Grubbs
Journal:  Acc Chem Res       Date:  2001-01       Impact factor: 22.384

2.  Shining new light on an old problem: retooling MALDI mass spectrometry for organotransition-metal catalysis.

Authors:  Melanie D Eelman; Johanna M Blacquiere; Maeve M Moriarty; Deryn E Fogg
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 3.  The remarkable metal-catalysed olefin metathesis reaction.

Authors:  Amir H Hoveyda; Adil R Zhugralin
Journal:  Nature       Date:  2007-11-08       Impact factor: 49.962

4.  Cationic Ru(II) complexes with N-heterocyclic carbene ligands for UV-induced ring-opening metathesis polymerization.

Authors:  Dongren Wang; Klaus Wurst; Wolfgang Knolle; Ulrich Decker; Lutz Prager; Sergej Naumov; Michael R Buchmeiser
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Organic Photoredox Catalysis.

Authors:  Nathan A Romero; David A Nicewicz
Journal:  Chem Rev       Date:  2016-06-10       Impact factor: 60.622

Review 6.  Olefin Metathesis at the Dawn of Implementation in Pharmaceutical and Specialty-Chemicals Manufacturing.

Authors:  Carolyn S Higman; Justin A M Lummiss; Deryn E Fogg
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-17       Impact factor: 15.336

7.  Cationic versus neutral Ru(II)--N-heterocyclic carbene complexes as latent precatalysts for the UV-induced ring-opening metathesis polymerization.

Authors:  Dongren Wang; Klaus Wurst; Michael R Buchmeiser
Journal:  Chemistry       Date:  2010-11-15       Impact factor: 5.236

8.  Metal-free ring-opening metathesis polymerization.

Authors:  Kelli A Ogawa; Adam E Goetz; Andrew J Boydston
Journal:  J Am Chem Soc       Date:  2015-01-21       Impact factor: 15.419

9.  Reactions of N-heterocyclic carbenes (NHCs) with one-electron oxidants: possible formation of a carbene cation radical.

Authors:  Taramatee Ramnial; Iain McKenzie; Brian Gorodetsky; Emily M W Tsang; Jason A C Clyburne
Journal:  Chem Commun (Camb)       Date:  2004-04-01       Impact factor: 6.222

10.  A Novel Class of Ruthenium Catalysts for Olefin Metathesis.

Authors:  Thomas Weskamp; Wolfgang C Schattenmann; Michael Spiegler; Wolfgang A Herrmann
Journal:  Angew Chem Int Ed Engl       Date:  1998-10-02       Impact factor: 15.336

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  8 in total

1.  The Janus face of high trans-effect carbenes in olefin metathesis: gateway to both productivity and decomposition.

Authors:  Giovanni Occhipinti; Daniel L Nascimento; Marco Foscato; Deryn E Fogg; Vidar R Jensen
Journal:  Chem Sci       Date:  2022-03-22       Impact factor: 9.969

2.  Hydrazone and Oxime Olefination via Ruthenium Alkylidenes.

Authors:  Daniel J Nasrallah; Troy E Zehnder; Jacob R Ludwig; Daniel C Steigerwald; John J Kiernicki; Nathaniel K Szymczak; Corinna S Schindler
Journal:  Angew Chem Int Ed Engl       Date:  2022-03-29       Impact factor: 16.823

3.  Combining a ligand photogenerator and a Ru precatalyst: a photoinduced approach to cross-linked ROMP polymer films.

Authors:  Thi Kim Hoang Trinh; Gautier Schrodj; Séverinne Rigolet; Julien Pinaud; Patrick Lacroix-Desmazes; Loic Pichavant; Valérie Héroguez; Abraham Chemtob
Journal:  RSC Adv       Date:  2019-09-04       Impact factor: 4.036

4.  Visible-Light-Initiated Palladium-Catalyzed Cross-coupling by PPh3 Uncaging from an Azobenzene Ruthenium-Arene Complex.

Authors:  Lou Rocard; Jérôme Hannedouche; Nicolas Bogliotti
Journal:  Chemistry       Date:  2022-06-10       Impact factor: 5.020

5.  Routes to High-Performing Ruthenium-Iodide Catalysts for Olefin Metathesis: Ligand Lability Is Key to Efficient Halide Exchange.

Authors:  Christian O Blanco; Daniel L Nascimento; Deryn E Fogg
Journal:  Organometallics       Date:  2021-06-16       Impact factor: 3.876

6.  Light-Activated Olefin Metathesis: Catalyst Development, Synthesis, and Applications.

Authors:  Or Eivgi; Ravindra S Phatake; Noy B Nechmad; N Gabriel Lemcoff
Journal:  Acc Chem Res       Date:  2020-09-29       Impact factor: 22.384

7.  Continuous Additive Manufacturing using Olefin Metathesis.

Authors:  Jeffrey C Foster; Adam W Cook; Nicolas T Monk; Brad H Jones; Leah N Appelhans; Erica M Redline; Samuel C Leguizamon
Journal:  Adv Sci (Weinh)       Date:  2022-03-10       Impact factor: 17.521

8.  Bimolecular Coupling in Olefin Metathesis: Correlating Structure and Decomposition for Leading and Emerging Ruthenium-Carbene Catalysts.

Authors:  Daniel L Nascimento; Marco Foscato; Giovanni Occhipinti; Vidar R Jensen; Deryn E Fogg
Journal:  J Am Chem Soc       Date:  2021-07-16       Impact factor: 15.419

  8 in total

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