Literature DB >> 21548658

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

Bruce H Lipshutz1, Subir Ghorai, Alexander R Abela, Ralph Moser, Takashi Nishikata, Christophe Duplais, Arkady Krasovskiy, Ricky D Gaston, Robert C Gadwood.   

Abstract

An environmentally benign surfactant (TPGS-750-M), a diester composed of racemic α-tocopherol, MPEG-750, and succinic acid, has been designed and readily prepared as an effective nanomicelle-forming species for general use in metal-catalyzed cross-coupling reactions in water. Several "name" reactions, including Heck, Suzuki-Miyaura, Sonogashira, and Negishi-like couplings, have been studied using this technology, as have aminations, C-H activations, and olefin metathesis reactions. Physical data in the form of DLS and cryo-TEM measurements suggest that particle size and shape are key elements in achieving high levels of conversion and, hence, good isolated yields of products. This new amphiphile will soon be commercially available.

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Year:  2011        PMID: 21548658      PMCID: PMC3608414          DOI: 10.1021/jo101974u

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  37 in total

1.  A novel polymer-supported arene-ruthenium complex for ring-closing olefin metathesis.

Authors:  Ryo Akiyama; Shū Kobayashi
Journal:  Angew Chem Int Ed Engl       Date:  2002-07-15       Impact factor: 15.336

2.  An extremely active catalyst for the Negishi cross-coupling reaction.

Authors:  Jacqueline E Milne; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

3.  Reactions in micellar systems.

Authors:  Torsten Dwars; Eckhard Paetzold; Günther Oehme
Journal:  Angew Chem Int Ed Engl       Date:  2005-11-11       Impact factor: 15.336

4.  Heck couplings at room temperature in nanometer aqueous micelles.

Authors:  Bruce H Lipshutz; Benjamin R Taft
Journal:  Org Lett       Date:  2008-03-12       Impact factor: 6.005

5.  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

6.  Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors:  Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

7.  Platinum-catalyzed direct amination of allylic alcohols under mild conditions: ligand and microwave effects, substrate scope, and mechanistic study.

Authors:  Takashi Ohshima; Yoshiki Miyamoto; Junji Ipposhi; Yasuhito Nakahara; Masaru Utsunomiya; Kazushi Mashima
Journal:  J Am Chem Soc       Date:  2009-10-14       Impact factor: 15.419

8.  An ionic liquid-supported ruthenium carbene complex: a robust and recyclable catalyst for ring-closing olefin metathesis in ionic liquids.

Authors:  Nicolas Audic; Hervé Clavier; Marc Mauduit; Jean-Claude Guillemin
Journal:  J Am Chem Soc       Date:  2003-08-06       Impact factor: 15.419

9.  Zn-mediated, Pd-catalyzed cross-couplings in water at room temperature without prior formation of organozinc reagents.

Authors:  Arkady Krasovskiy; Christophe Duplais; Bruce H Lipshutz
Journal:  J Am Chem Soc       Date:  2009-11-04       Impact factor: 15.419

10.  Direct coupling of benzene with olefin catalyzed by Pd(OAc)(2) combined with heteropolyoxometalate under dioxygen.

Authors:  Takahiro Yokota; Masayuki Tani; Satoshi Sakaguchi; Yasutaka Ishii
Journal:  J Am Chem Soc       Date:  2003-02-12       Impact factor: 15.419

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  37 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.  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

3.  Synthesis, characterization, and in-vitro antitumor activity of the polyethylene glycol (350 and 1000) succinate derivatives of the tocopherol and tocotrienol isomers of Vitamin E.

Authors:  Ahmed Abu-Fayyad; Sami Nazzal
Journal:  Int J Pharm       Date:  2017-01-16       Impact factor: 5.875

4.  "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

5.  Aerobic oxidation in nanomicelles of aryl alkynes, in water at room temperature.

Authors:  Sachin Handa; James C Fennewald; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-24       Impact factor: 15.336

6.  "Click" and Olefin Metathesis Chemistry in Water at Room Temperature Enabled by Biodegradable Micelles.

Authors:  Bruce H Lipshutz; Zarko Bošković; Christopher S Crowe; Victoria K Davis; Hannah C Whittemore; David A Vosburg; Anna G Wenzel
Journal:  J Chem Educ       Date:  2013-11-12       Impact factor: 2.979

7.  Transitioning organic synthesis from organic solvents to water. What's your E Factor?

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Green Chem       Date:  2014-08-01       Impact factor: 10.182

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

9.  Installation of protected ammonia equivalents onto aromatic & heteroaromatic rings in water enabled by micellar catalysis.

Authors:  Nicholas A Isley; Sebastian Dobarco; Bruce H Lipshutz
Journal:  Green Chem       Date:  2014-01-02       Impact factor: 10.182

10.  Catalysis in the Service of Green Chemistry: Nobel Prize-Winning Palladium-Catalysed Cross-Couplings, Run in Water at Room Temperature: Heck, Suzuki-Miyaura and Negishi reactions carried out in the absence of organic solvents, enabled by micellar catalysis.

Authors:  Bruce H Lipshutz; Benjamin R Taft; Alexander R Abela; Subir Ghorai; Arkady Krasovskiy; Christophe Duplais
Journal:  Platin Met Rev       Date:  2012-04
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