Literature DB >> 25170307

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

Bruce H Lipshutz1, Subir Ghorai2.   

Abstract

Traditional organic chemistry, and organic synthesis in particular, relies heavily on organic solvents, as most reactions involve organic substrates and catalysts that tend to be water-insoluble. Unfortunately, organic solvents make up most of the organic waste created by the chemical enterprise, whether from academic, industrial, or governmental labs. One alternative to organic solvents follows the lead of Nature: water. To circumvent the solubility issues, newly engineered "designer" surfactants offer an opportunity to efficiently enable many of the commonly used transition metal-catalyzed and related reactions in organic synthesis to be run in water, and usually at ambient temperatures. This review focuses on recent progress in this area, where such amphiphiles spontaneously self-aggregate in water. The resulting micellar arrays serve as nanoreactors, obviating organic solvents as the reaction medium, while maximizing environmental benefits.

Entities:  

Year:  2014        PMID: 25170307      PMCID: PMC4142526          DOI: 10.1039/C4GC00503A

Source DB:  PubMed          Journal:  Green Chem        ISSN: 1463-9262            Impact factor:   10.182


  66 in total

1.  Selective palladium-catalyzed arylation of ammonia: synthesis of anilines as well as symmetrical and unsymmetrical di- and triarylamines.

Authors:  David S Surry; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2007-08-02       Impact factor: 15.419

2.  Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize.

Authors:  Carin C C Johansson Seechurn; Matthew O Kitching; Thomas J Colacot; Victor Snieckus
Journal:  Angew Chem Int Ed Engl       Date:  2012-05-09       Impact factor: 15.336

3.  Miyaura Borylations of Aryl Bromides in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Ralph Moser; Karl R Voigtritter
Journal:  Isr J Chem       Date:  2010-12-01       Impact factor: 3.333

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

Review 5.  Phytosterols, phytostanols, and their conjugates in foods: structural diversity, quantitative analysis, and health-promoting uses.

Authors:  Robert A Moreau; Bruce D Whitaker; Kevin B Hicks
Journal:  Prog Lipid Res       Date:  2002-11       Impact factor: 16.195

6.  Room-temperature Pd-catalyzed amidation of aryl bromides using tert-butyl carbamate.

Authors:  Swapna Bhagwanth; Alex G Waterson; George M Adjabeng; Keith R Hornberger
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354

Review 7.  Potential uses and benefits of phytosterols in diet: present situation and future directions.

Authors:  J QuIlez; P GarcIa-Lorda; J Salas-Salvadó
Journal:  Clin Nutr       Date:  2003-08       Impact factor: 7.324

Review 8.  Phytosterols: physiologic and metabolic aspects related to cholesterol-lowering properties.

Authors:  Gemma Brufau; Miguel Angel Canela; Magda Rafecas
Journal:  Nutr Res       Date:  2008-04       Impact factor: 3.315

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.  Transforming Suzuki-Miyaura cross-couplings of MIDA boronates into a green technology: no organic solvents.

Authors:  Nicholas A Isley; Fabrice Gallou; Bruce H Lipshutz
Journal:  J Am Chem Soc       Date:  2013-11-13       Impact factor: 15.419

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  13 in total

Review 1.  Cascade Processes with Micellar Reaction Media: Recent Advances and Future Directions.

Authors:  Christina Tang; Bridget T McInnes
Journal:  Molecules       Date:  2022-08-31       Impact factor: 4.927

Review 2.  Photochemical Approaches to Complex Chemotypes: Applications in Natural Product Synthesis.

Authors:  Markus D Kärkäs; John A Porco; Corey R J Stephenson
Journal:  Chem Rev       Date:  2016-04-27       Impact factor: 60.622

3.  Metal-free O-H/C-H difunctionalization of phenols by o-hydroxyarylsulfonium salts in water.

Authors:  Dengfeng Chen; Qingyuan Feng; Yunqin Yang; Xu-Min Cai; Fei Wang; Shenlin Huang
Journal:  Chem Sci       Date:  2016-11-04       Impact factor: 9.825

4.  Water opens the door to organolithiums and Grignard reagents: exploring and comparing the reactivity of highly polar organometallic compounds in unconventional reaction media towards the synthesis of tetrahydrofurans.

Authors:  Luciana Cicco; Stefania Sblendorio; Rosmara Mansueto; Filippo M Perna; Antonio Salomone; Saverio Florio; Vito Capriati
Journal:  Chem Sci       Date:  2015-11-03       Impact factor: 9.825

5.  Transformation of Tertiary Benzyl Alcohols into the Vicinal Halo-Substituted Derivatives Using N-Halosuccinimides.

Authors:  Njomza Ajvazi; Stojan Stavber
Journal:  Molecules       Date:  2016-10-02       Impact factor: 4.411

Review 6.  Recent advances in Cu-catalyzed C(sp3)-Si and C(sp3)-B bond formation.

Authors:  Balaram S Takale; Ruchita R Thakore; Elham Etemadi-Davan; Bruce H Lipshutz
Journal:  Beilstein J Org Chem       Date:  2020-04-15       Impact factor: 2.883

7.  Reshaping Ullmann Amine Synthesis in Deep Eutectic Solvents: A Mild Approach for Cu-Catalyzed C-N Coupling Reactions With No Additional Ligands.

Authors:  Andrea Francesca Quivelli; Paola Vitale; Filippo Maria Perna; Vito Capriati
Journal:  Front Chem       Date:  2019-10-30       Impact factor: 5.221

8.  Palladium (II)-Salan Complexes as Catalysts for Suzuki-Miyaura C-C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance.

Authors:  Szilvia Bunda; Krisztina Voronova; Ágnes Kathó; Antal Udvardy; Ferenc Joó
Journal:  Molecules       Date:  2020-09-02       Impact factor: 4.411

9.  Sustainable Access to π-Conjugated Molecular Materials via Direct (Hetero)Arylation Reactions in Water and under Air.

Authors:  Adiel Mauro Calascibetta; Sara Mattiello; Alessandro Sanzone; Irene Facchinetti; Mauro Sassi; Luca Beverina
Journal:  Molecules       Date:  2020-08-14       Impact factor: 4.411

10.  Surface-active ionic liquids in micellar catalysis: impact of anion selection on reaction rates in nucleophilic substitutions.

Authors:  Alice Cognigni; Peter Gaertner; Ronald Zirbs; Herwig Peterlik; Katharina Prochazka; Christian Schröder; Katharina Bica
Journal:  Phys Chem Chem Phys       Date:  2016-04-28       Impact factor: 3.676

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