Literature DB >> 20882969

Stereoselective Negishi-like couplings between alkenyl and alkyl halides in water at room temperature.

Arkady Krasovskiy1, Christophe Duplais, Bruce H Lipshutz.   

Abstract

Mix in water and then stir. That is all that is required in this new approach to stereoselective sp(3)-sp(2) cross-couplings between an alkyl and alkenyl halide. Prior formation of organozinc reagents is not required.

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Year:  2010        PMID： 20882969      PMCID： PMC3365513          DOI： 10.1021/ol101885t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  2 in total

1.  Recent advances in efficient and selective synthesis of di-, tri-, and tetrasubstituted alkenes via Pd-catalyzed alkenylation-carbonyl olefination synergy.

Authors:  Ei-ichi Negishi; Zhihong Huang; Guangwei Wang; Swathi Mohan; Chao Wang; Hatsuhiko Hattori
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

2.  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
  2 in total
  15 in total

1.  "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

Authors:  Bruce H Lipshutz; Subir Ghorai
Journal:  Aldrichimica Acta       Date:  2012-01-01       Impact factor: 3.667

2.  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

3.  "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

4.  Cross-Electrophile Coupling of Vinyl Halides with Alkyl Halides.

Authors:  Keywan A Johnson; Soumik Biswas; Daniel J Weix
Journal:  Chemistry       Date:  2016-04-28       Impact factor: 5.236

5.  Reductive Decarboxylative Alkynylation of N-Hydroxyphthalimide Esters with Bromoalkynes.

Authors:  Liangbin Huang; Astrid M Olivares; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       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.  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

8.  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

9.  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.

Authors:  Bruce H Lipshutz; Benjamin R Taft; Alexander R Abela; Subir Ghorai; Arkady Krasovskiy; Christophe Duplais
Journal:  Platin Met Rev       Date:  2012-04

10.  Alkenylation of C(sp3 )-H Bonds by Zincation/Copper-Catalyzed Cross-Coupling with Iodonium Salts.

Authors:  Chuan Liu; Qiu Wang
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-15       Impact factor: 15.336
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