Literature DB >> 21487612

"On water" sp3-sp2 cross-couplings between benzylic and alkenyl halides.

Valeria Krasovskaya1, Arkady Krasovskiy, Anish Bhattacharjya, Bruce H Lipshutz.   

Abstract

Organic-solvent-free cross-couplings between benzylic and alkenyl halides have been developed. Various alkenyl halides can be efficiently benzylated by combining the precursor halides in the presence of Zn dust and a Pd catalyst at room temperature, in water as the only medium. © The Royal Society of Chemistry 2011

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Year:  2011        PMID: 21487612      PMCID: PMC3352766          DOI: 10.1039/c1cc11087j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  22 in total

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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
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3.  Suzuki-Miyaura cross-coupling of benzylic carbonates with arylboronic acids.

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Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

4.  Simple (imidazol-2-ylidene)-Pd-acetate complexes as effective precatalysts for sterically hindered Suzuki-Miyaura couplings.

Authors:  Rohit Singh; Mihai S Viciu; Natalia Kramareva; Oscar Navarro; Steven P Nolan
Journal:  Org Lett       Date:  2005-04-28       Impact factor: 6.005

5.  Copper-mediated cross-coupling of functionalized arylmagnesium reagents with functionalized alkyl and benzylic halides.

Authors:  W Dohle; D M Lindsay; P Knochel
Journal:  Org Lett       Date:  2001-09-06       Impact factor: 6.005

6.  Suzuki-Miyaura cross-coupling reactions of benzyl halides with potassium aryltrifluoroborates.

Authors:  Gary A Molander; Maxwell D Elia
Journal:  J Org Chem       Date:  2006-11-24       Impact factor: 4.354

7.  Palladium-catalyzed cross-coupling of B-benzyl-9-borabicyclo[3.3.1]nonane to furnish methylene-linked biaryls.

Authors:  Alice Flaherty; Amy Trunkfield; William Barton
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

8.  Suzuki-Miyaura cross-coupling of benzylic phosphates with arylboronic acids.

Authors:  Mark McLaughlin
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

9.  Iron-catalysed Negishi coupling of benzyl halides and phosphates.

Authors:  Robin B Bedford; Michael Huwe; Mark C Wilkinson
Journal:  Chem Commun (Camb)       Date:  2008-12-11       Impact factor: 6.222

10.  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

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  8 in total

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Authors:  Liangbin Huang; Astrid M Olivares; Daniel J Weix
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4.  Photodegradable Antimicrobial Agents: Synthesis and Mechanism of Degradation.

Authors:  Vebjørn Eikemo; Bjarte Holmelid; Leiv K Sydnes; Magne O Sydnes
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5.  Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature.

Authors:  Christophe Duplais; Arkady Krasovskiy; Bruce H Lipshutz
Journal:  Organometallics       Date:  2011-11-21       Impact factor: 3.876

6.  Replacing conventional carbon nucleophiles with electrophiles: nickel-catalyzed reductive alkylation of aryl bromides and chlorides.

Authors:  Daniel A Everson; Brittany A Jones; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2012-03-30       Impact factor: 15.419

7.  Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides.

Authors:  Laura K G Ackerman; Lukiana L Anka-Lufford; Marina Naodovic; Daniel J Weix
Journal:  Chem Sci       Date:  2014-11-10       Impact factor: 9.825

8.  Kumada-Grignard-type biaryl couplings on water.

Authors:  Anish Bhattacharjya; Piyatida Klumphu; Bruce H Lipshutz
Journal:  Nat Commun       Date:  2015-06-18       Impact factor: 14.919

  8 in total

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