Literature DB >> 18335945

Heck couplings at room temperature in nanometer aqueous micelles.

Bruce H Lipshutz1, Benjamin R Taft.   

Abstract

A nonionic amphiphile such as Triton X-100 or the vitamin E-based PTS, both of which form nanomicelles in water, promotes Heck cross-couplings of non-water-soluble partners at ambient temperatures. These are the first examples of Heck reactions conducted in water (as the only solvent) at room temperature.

Entities:  

Year:  2008        PMID: 18335945     DOI: 10.1021/ol702755g

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


  15 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.  Allylic ethers as educts for Suzuki-Miyaura couplings in water at room temperature.

Authors:  Takashi Nishikata; Bruce H Lipshutz
Journal:  J Am Chem Soc       Date:  2009-09-02       Impact factor: 15.419

3.  Storable arylpalladium(II) reagents for alkene labeling in aqueous media.

Authors:  Rebecca L Simmons; Robert T Yu; Andrew G Myers
Journal:  J Am Chem Soc       Date:  2011-09-15       Impact factor: 15.419

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.  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 9.  Organic synthesis "on water".

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

10.  Trifluoromethylation of Heterocycles in Water at Room Temperature.

Authors:  James C Fennewald; Bruce H Lipshutz
Journal:  Green Chem       Date:  2014-03-01       Impact factor: 10.182

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