Literature DB >> 23555153

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.

Bruce H Lipshutz1, Benjamin R Taft, Alexander R Abela, Subir Ghorai, Arkady Krasovskiy, Christophe Duplais.   

Abstract

Palladium-catalysed cross-couplings, in particular Heck, Suzuki-Miyaura and Negishi reactions developed over three decades ago, are routinely carried out in organic solvents. However, alternative media are currently of considerable interest given an increasing emphasis on making organic processes 'greener'; for example, by minimising organic waste in the form of organic solvents. Water is the obvious leading candidate in this regard. Hence, this review focuses on the application of micellar catalysis, in which a 'designer' surfactant enables these award-winning coupling reactions to be run in water at room temperature.

Entities:  

Year:  2012        PMID: 23555153      PMCID: PMC3608409          DOI: 10.1595/147106712x629761

Source DB:  PubMed          Journal:  Platin Met Rev        ISSN: 0032-1400


  26 in total

1.  Ionic liquid (molten salt) phase organometallic catalysis.

Authors:  Jairton Dupont; Roberto F de Souza; Paulo A Z Suarez
Journal:  Chem Rev       Date:  2002-10       Impact factor: 60.622

2.  Ionic Liquids-New "Solutions" for Transition Metal Catalysis.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-11-03       Impact factor: 15.336

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.  Direct synthesis of propylene oxide with CO2 as the solvent.

Authors:  Tiberiu Danciu; Eric J Beckman; Dan Hancu; Robert N Cochran; Roger Grey; Dennis M Hajnik; Jennifer Jewson
Journal:  Angew Chem Int Ed Engl       Date:  2003-03-10       Impact factor: 15.336

5.  New air-stable catalysts for general and efficient suzuki-miyaura cross-coupling reactions of heteroaryl chlorides.

Authors:  Anil S Guram; Anthony O King; John G Allen; Xianghong Wang; Laurie B Schenkel; Johann Chan; Emilio E Bunel; Margaret M Faul; Robert D Larsen; Michael J Martinelli; Paul J Reider
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

6.  Ligand effects on Negishi couplings of alkenyl halides.

Authors:  Arkady Krasovskiy; Bruce H Lipshutz
Journal:  Org Lett       Date:  2011-07-08       Impact factor: 6.005

7.  Highly selective reactions of unbiased alkenyl halides and alkylzinc halides: Negishi-Plus couplings.

Authors:  Arkady Krasovskiy; Bruce H Lipshutz
Journal:  Org Lett       Date:  2011-07-08       Impact factor: 6.005

8.  Cp2Fe(PR2)2PdCl2 (R = i-Pr, t-Bu) complexes as air-stable catalysts for challenging Suzuki coupling reactions.

Authors:  Thomas J Colacot; Helene A Shea
Journal:  Org Lett       Date:  2004-10-14       Impact factor: 6.005

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.  Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions.

Authors:  Nicolas Marion; Oscar Navarro; Jianguo Mei; Edwin D Stevens; Natalie M Scott; Steven P Nolan
Journal:  J Am Chem Soc       Date:  2006-03-29       Impact factor: 15.419

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  3 in total

1.  Single-Micelle and Single-Zinc-Particle Imaging Provides Insights into the Physical Processes Underpinning Organozinc Reactions in Water.

Authors:  Hannah Peacock; Suzanne A Blum
Journal:  J Am Chem Soc       Date:  2022-02-14       Impact factor: 15.419

Review 2.  Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives.

Authors:  Andrew Jordan; Callum G J Hall; Lee R Thorp; Helen F Sneddon
Journal:  Chem Rev       Date:  2022-02-24       Impact factor: 72.087

3.  Efficient Suzuki⁻Miyaura C-C Cross-Couplings Induced by Novel Heterodinuclear Pd-bpydc-Ln Scaffolds.

Authors:  Fu Ding; Yanli Li; Pingxuan Yan; Yan Deng; Dongping Wang; Yajing Zhang; Ileana Dragutan; Valerian Dragutan; Kangjun Wang
Journal:  Molecules       Date:  2018-09-23       Impact factor: 4.411

  3 in total

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