Literature DB >> 24030905

On the way towards greener transition-metal-catalyzed processes as quantified by E factors.

Bruce H Lipshutz1, Nicholas A Isley, James C Fennewald, Eric D Slack.   

Abstract

Transition-metal-catalyzed carbon-carbon and carbon-heteroatom bond formations are among the most heavily used types of reactions in both academic and industrial settings. As important as these are to the synthetic community, such cross-couplings come with a heavy price to our environment, and sustainability. E Factors are one measure of waste created, and organic solvents, by far, are the main contributors to the high values associated, in particular, with the pharmaceutical and fine-chemical companies which utilize these reactions. An alternative to organic solvents in which cross-couplings are run can be found in the form of micellar catalysis, wherein nanoparticles composed of newly introduced designer surfactants enable the same cross-couplings, albeit in water, with most taking place at room temperature. In the absence of an organic solvent as the reaction medium, organic waste and hence, E Factors, drop dramatically.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  E Factors; cross-coupling; green chemistry; micelles; water chemistry

Mesh:

Substances:

Year:  2013        PMID: 24030905      PMCID: PMC4068147          DOI: 10.1002/anie.201302020

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  14 in total

Review 1.  Industrial applications using BASF eco-efficiency analysis: perspectives on green engineering principles.

Authors:  David R Shonnard; Andreas Kicherer; Peter Saling
Journal:  Environ Sci Technol       Date:  2003-12-01       Impact factor: 9.028

Review 2.  Hydrophobically directed organic synthesis.

Authors:  Ulf M Lindström; Fredrik Andersson
Journal:  Angew Chem Int Ed Engl       Date:  2006-01-16       Impact factor: 15.336

3.  Scalable synthesis and isolation of the four stereoisomers of methyl 1-amino-3-(4-bromophenyl)cyclopentanecarboxylate, useful intermediates for the synthesis of S1P1 receptor agonists.

Authors:  Grier A Wallace; Thomas D Gordon; Martin E Hayes; Donald B Konopacki; Shannon R Fix-Stenzel; Xiaolei Zhang; Pintipa Grongsaard; Kevin P Cusack; Lisa M Schaffter; Rodger F Henry; Robert H Stoffel
Journal:  J Org Chem       Date:  2009-07-03       Impact factor: 4.354

4.  PQS: a new platform for micellar catalysis. RCM reactions in water, with catalyst recycling.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Org Lett       Date:  2009-02-05       Impact factor: 6.005

5.  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

6.  Rhodium-Catalyzed Asymmetric 1,4-Additions, in Water at Room Temperature, with In-Flask Catalyst Recycling.

Authors:  Bruce H Lipshutz; Nicholas A Isley; Ralph Moser; Subir Ghorai; Helena Leuser; Benjamin R Taft
Journal:  Adv Synth Catal       Date:  2012-11-26       Impact factor: 5.837

Review 7.  Large-scale applications of transition metal-catalyzed couplings for the synthesis of pharmaceuticals.

Authors:  Javier Magano; Joshua R Dunetz
Journal:  Chem Rev       Date:  2011-03-09       Impact factor: 60.622

8.  Organocatalysis in water at room temperature with in-flask catalyst recycling.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Org Lett       Date:  2011-12-19       Impact factor: 6.005

9.  Modified routes to the "designer" surfactant PQS.

Authors:  Ralph Moser; Subir Ghorai; Bruce H Lipshutz
Journal:  J Org Chem       Date:  2012-03-13       Impact factor: 4.354

10.  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

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  18 in total

1.  Asymmetric gold-catalyzed lactonizations in water at room temperature.

Authors:  Sachin Handa; Daniel J Lippincott; Donald H Aue; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2014-08-14       Impact factor: 15.336

2.  HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature.

Authors:  Sachin Handa; Martin P Andersson; Fabrice Gallou; John Reilly; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-29       Impact factor: 15.336

3.  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

4.  Dehalogenation of Functionalized Alkyl Halides in Water at Room Temperature.

Authors:  Nicholas A Isley; Matt S Hageman; Bruce H Lipshutz
Journal:  Green Chem       Date:  2015       Impact factor: 10.182

5.  A palladium nanoparticle-nanomicelle combination for the stereoselective semihydrogenation of alkynes in water at room temperature.

Authors:  Eric D Slack; Christopher M Gabriel; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2014-10-16       Impact factor: 15.336

6.  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

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.  Nanonickel-catalyzed Suzuki-Miyaura cross-couplings in water.

Authors:  Sachin Handa; Eric D Slack; Bruce H Lipshutz
Journal:  Angew Chem Int Ed Engl       Date:  2015-08-25       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.  Chemoselective reductions of nitroaromatics in water at room temperature.

Authors:  Sean M Kelly; Bruce H Lipshutz
Journal:  Org Lett       Date:  2013-12-16       Impact factor: 6.005

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