Literature DB >> 18335947

Olefin cross-metathesis reactions at room temperature using the nonionic amphiphile "PTS": just add water.

Bruce H Lipshutz1, Grant T Aguinaldo, Subir Ghorai, Karl Voigtritter.   

Abstract

The first examples of unsymmetrical olefin cross-metathesis reactions in water, involving water-insoluble substrates, at room temperature and using commercially available catalysts are reported. The key to success is to include small percentages of the nonionic, vitamin E-based amphiphile "PTS". The nanometer micelles formed accommodate water-insoluble substrates, along with a readily available Ru-based metathesis catalyst. Reactions proceed at ambient temperatures with high efficiency and very high E-selectivity, and products are easily isolated.

Entities:  

Year:  2008        PMID： 18335947     DOI： 10.1021/ol800028x

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  20 in total

1.  "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

2.  "Nok": a phytosterol-based amphiphile enabling transition-metal-catalyzed couplings in water at room temperature.

Authors:  Piyatida Klumphu; Bruce H Lipshutz
Journal:  J Org Chem       Date:  2014-01-21       Impact factor: 4.354

3.  Electrophilic aromatic prenylation via cascade cyclization.

Authors:  John G Kodet; Joseph J Topczewski; Kevyn D Gardner; David F Wiemer
Journal:  Tetrahedron       Date:  2013-10-04       Impact factor: 2.457

4.  Aminations of Aryl Bromides in Water at Room Temperature.

Authors:  Bruce H Lipshutz; David W Chung; Brian Rich
Journal:  Adv Synth Catal       Date:  2009-08       Impact factor: 5.837

5.  Manipulating micellar environments for enhancing transition metal-catalyzed cross-couplings in water at room temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai; Wendy Wen Yi Leong; Benjamin R Taft; Daniel V Krogstad
Journal:  J Org Chem       Date:  2011-05-19       Impact factor: 4.354

6.  TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai; Alexander R Abela; Ralph Moser; Takashi Nishikata; Christophe Duplais; Arkady Krasovskiy; Ricky D Gaston; Robert C Gadwood
Journal:  J Org Chem       Date:  2011-05-09       Impact factor: 4.354

7.  Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature.

Authors:  Stefan R K Minkler; Nicholas A Isley; Daniel J Lippincott; Norbert Krause; Bruce H Lipshutz
Journal:  Org Lett       Date:  2014-01-16       Impact factor: 6.005

8.  Ring opening metathesis polymerization-derived block copolymers bearing chelating ligands: synthesis, metal immobilization and use in hydroformylation under micellar conditions.

Authors:  Gajanan M Pawar; Jochen Weckesser; Siegfried Blechert; Michael R Buchmeiser
Journal:  Beilstein J Org Chem       Date:  2010-03-23       Impact factor: 2.883

9.  Designer Micelles Accelerate Flux Through Engineered Metabolism in E. coli and Support Biocompatible Chemistry.

Authors:  Stephen Wallace; Emily P Balskus
Journal:  Angew Chem Int Ed Engl       Date:  2016-04-08       Impact factor: 15.336

Review 10.  Organic synthesis "on water".

Authors:  Arani Chanda; Valery V Fokin
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622
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