Literature DB >> 21739948

Ligand effects on Negishi couplings of alkenyl halides.

Arkady Krasovskiy1, Bruce H Lipshutz.   

Abstract

Negishi couplings at olefinic centers do not always occur with the anticipated maintenance of stereochemistry. The source of erosion has been traced to the ligand, and a modified method has been developed that solves the stereochemical issue and significantly improves yields of Negishi couplings in general.
© 2011 American Chemical Society

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Year:  2011        PMID： 21739948      PMCID： PMC3365518          DOI： 10.1021/ol2010165

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


  13 in total

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2.  In situ generated bulky palladium hydride complexes as catalysts for the efficient isomerization of olefins. Selective transformation of terminal alkenes to 2-alkenes.

Authors:  Delphine Gauthier; Anders T Lindhardt; Esben P K Olsen; Jacob Overgaard; Troels Skrydstrup
Journal:  J Am Chem Soc       Date:  2010-06-16       Impact factor: 15.419

3.  Kumada coupling of aryl and vinyl tosylates under mild conditions.

Authors:  Michael E Limmert; Amy H Roy; John F Hartwig
Journal:  J Org Chem       Date:  2005-11-11       Impact factor: 4.354

4.  Studies on the Heck reaction with alkenyl phosphates: can the 1,2-migration be controlled? Scope and limitations.

Authors:  Jean-Philippe Ebran; Anders L Hansen; Thomas M Gøgsig; Troels Skrydstrup
Journal:  J Am Chem Soc       Date:  2007-05-03       Impact factor: 15.419

5.  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

6.  Ligand effects on the Pd-catalyzed cross-coupling reaction of 3-iodoalk-2-enoates with propargyl/1,2-allenylic metallic species: an efficient regiodivergent synthesis of 2,4,5-trienoates.

Authors:  Jinbo Zhao; Yihua Yu; Shengming Ma
Journal:  Chemistry       Date:  2010-01-04       Impact factor: 5.236

7.  Revealing a second transmetalation step in the Negishi coupling and its competition with reductive elimination: improvement in the interpretation of the mechanism of biaryl syntheses.

Authors:  Qiang Liu; Yu Lan; Jing Liu; Gang Li; Yun-Dong Wu; Aiwen Lei
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419

8.  Elucidating reactivity differences in palladium-catalyzed coupling processes: the chemistry of palladium hydrides.

Authors:  Ivory D Hills; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2004-10-20       Impact factor: 15.419

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.  What is the rate of the Csp2-Csp2 reductive elimination step? Revealing an unusually fast Ni-catalyzed Negishi-type oxidative coupling reaction.

Authors:  Liqun Jin; Hua Zhang; Peng Li; John R Sowa; Aiwen Lei
Journal:  J Am Chem Soc       Date:  2009-07-29       Impact factor: 15.419
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  4 in total

1.  Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.

Authors:  Beryl X Li; Diane N Le; Kyle A Mack; Andrew McClory; Ngiap-Kie Lim; Theresa Cravillion; Scott Savage; Chong Han; David B Collum; Haiming Zhang; Francis Gosselin
Journal:  J Am Chem Soc       Date:  2017-07-26       Impact factor: 15.419

2.  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

3.  Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

Authors:  Steffen Dachwitz; Bjarne Scharkowski; Norbert Sewald
Journal:  Chemistry       Date:  2021-11-11       Impact factor: 5.020

Review 4.  Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.

Authors:  Christopher S Horbaczewskyj; Ian J S Fairlamb
Journal:  Org Process Res Dev       Date:  2022-07-11       Impact factor: 3.858
  4 in total

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