Literature DB >> 20062862

Cross-couplings between benzylic and aryl halides "on water": synthesis of diarylmethanes.

Christophe Duplais1, Arkady Krasovskiy, Alina Wattenberg, Bruce H Lipshutz.   

Abstract

A remarkably simple entry to unsymmetrical diarylmethanes has been developed that relies on an in situ organozinc-mediated, palladium-catalyzed cross-coupling. Thus, by mixing a benzyl and aryl halide together in the presence of Zn metal and a Pd catalyst, diarylmethanes are formed at room temperature without assistance by a surfactant; hence, "on water".

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Year:  2009        PMID： 20062862      PMCID： PMC3152455          DOI： 10.1039/b922280d

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


  25 in total

1.  Structure-activity relationship of cinnamic acylsulfonamide analogues on the human EP3 prostanoid receptor.

Authors:  H Juteau; Y Gareau; M Labelle; C F Sturino; N Sawyer; N Tremblay; S Lamontagne; M C Carrière; D Denis; K M Metters
Journal:  Bioorg Med Chem       Date:  2001-08       Impact factor: 3.641

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

Authors:  Ryoichi Kuwano; Masashi Yokogi
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

3.  Conformationally restricted analogues of trimethoprim: 2,6-diamino-8-substituted purines as potential dihydrofolate reductase inhibitors from Pneumocystis carinii and Toxoplasma gondii.

Authors:  A Gangjee; A Vasudevan; S F Queener
Journal:  J Med Chem       Date:  1997-09-12       Impact factor: 7.446

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.  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

7.  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

8.  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

Review 9.  Organic synthesis "on water".

Authors:  Arani Chanda; Valery V Fokin
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622

10.  Preliminary in vitro studies on two potent, water-soluble trimethoprim analogues with exceptional species selectivity against dihydrofolate reductase from Pneumocystis carinii and Mycobacterium avium.

Authors:  Ronald A Forsch; Sherry F Queener; Andre Rosowsky
Journal:  Bioorg Med Chem Lett       Date:  2004-04-05       Impact factor: 2.823
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  9 in total

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

Authors:  Valeria Krasovskaya; Arkady Krasovskiy; Anish Bhattacharjya; Bruce H Lipshutz
Journal:  Chem Commun (Camb)       Date:  2011-04-12       Impact factor: 6.222

2.  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

3.  Nickel-Catalyzed Cross-Coupling of Aryl Halides with Alkyl Halides: Ethyl 4-(4-(4-methylphenylsulfonamido)-phenyl)butanoate.

Authors:  Daniel A Everson; David T George; Daniel J Weix; Jonas F Buergler; John L Wood
Journal:  Organic Synth       Date:  2013

4.  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

5.  Cation-π Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts.

Authors:  Sheng-Chun Sha; Sergei Tcyrulnikov; Minyan Li; Bowen Hu; Yue Fu; Marisa C Kozlowski; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2018-09-19       Impact factor: 15.419

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

Review 9.  Nanoreactors for green catalysis.

Authors:  M Teresa De Martino; Loai K E A Abdelmohsen; Floris P J T Rutjes; Jan C M van Hest
Journal:  Beilstein J Org Chem       Date:  2018-03-29       Impact factor: 2.883
  9 in total

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